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CAS 15690-38-7
(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidHydroxymethyl-7-aminocephalosporanicacid(6R,7R)-7-Amino-3-(hydroxymethyl)-3-cephem-4-carboxylicacid
Codes: Cefcamate Pivoxil Hydrochloride-005
Application context (from source-drug indications)
Bacterial infectionCefcamate Pivoxil Hydrochloride
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Cefcamate Pivoxil Hydrochloride | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
Cefcamate Pivoxil HydrochlorideOptimised routesteps: 7total yield: 120.1g(Cefcamate Pivoxil Hydrochloride (API))
Ethyl2-(bromoacetyl)pent-2-enoate→tert-Butylcarbamothioylcarbamatehydrobromide→Ethyl(2Z)-2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoate→2-[2(Z)-2-Boc-amino-1,3-thiazol-4-yl]pent-2-enoicacid→(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidN,N,N',N'-tetramethylguanidine(11)→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→Chlorosulfonicacidisocyanate→Trichloroacetylisocyanate→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidN-(propan-2-yl)propan-2-amine→Sodium(6R,7R)-7-[[(2Z)-2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→(6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-pentenoylamino]-3-(carbamoyloxymethyl)-3-cephem-4-carboxylicacid→(6R,7R)-7-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidhydrogenchloride→Iodomethylpivalate→[(2,2-Dimethylpropanoyl)oxy]methyl(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Cefcamate Pivoxil HydrochlorideOptimised routesteps: 5total yield: 23.5g(Cefcamate Pivoxil Hydrochloride-013)
(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→Chlorosulfonicacidisocyanate→(6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-pentenoylamino]-3-(carbamoyloxymethyl)-3-cephem-4-carboxylicacid→Methyl(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoate→Methyl(2Z)-2-[2-(2-phenylacetamido)-1,3-thiazol-4-yl]pent-2-enoate→(2Z)-2-[2-(2-Phenylacetamido)-1,3-thiazol-4-yl]pent-2-enoicacid→(6R)-3-[(Carbamoyloxy)methyl]-8-oxo-7-([(2Z)-2-[2-(2-phenylacetamido)-1,3-thiazol-4-yl]pent-2-enoyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid--N-(propan-2-yl)propan-2-amine(11)→Sodium(6R)-3-[(carbamoyloxy)methyl]-8-oxo-7-([(2Z)-2-[2-(2-phenylacetamido)-1,3-thiazol-4-yl]pent-2-enoyl]amino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Cefcamate Pivoxil HydrochlorideOptimised routesteps: 7total yield: 6.375g(Cefcamate Pivoxil Hydrochloride (API))
Ethyl2-(bromoacetyl)pent-2-enoate→tert-Butylcarbamothioylcarbamatehydrobromide→Ethyl(2Z)-2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoate→2-[2(Z)-2-Boc-amino-1,3-thiazol-4-yl]pent-2-enoicacid→(6R,7R)-7-Amino-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→Sodium(6R,7R)-7-[[(2Z)-2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→(6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-pentenoylamino]-3-(carbamoyloxymethyl)-3-cephem-4-carboxylicacid→(6R,7R)-7-[[(2Z)-2-(2-Amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidhydrogenchloride→Iodomethylpivalate→[(2,2-Dimethylpropanoyl)oxy]methyl(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Cefcamate Pivoxil HydrochlorideOptimised routesteps: 8total yield: 14.6g(Cefcamate Pivoxil Hydrochloride (API))
2-[2(Z)-2-Boc-amino-1,3-thiazol-4-yl]pent-2-enoicacid→tert-Butyl[4-[(2Z)-1-oxo-1-[(methylsulfonyl)oxy]pent-2-en-2-yl]-1,3-thiazol-2-yl]carbamate→Methyl(2Z)-2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoatehydrogenchloride→(6R,7R)-3-(Acetoxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid→(6R,7R)-3-[(Acetyloxy)methyl]-7-[[(2Z)-2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid→Hydroxymethyl-7-aminocephalosporanicacid→N-Carbonylsulfamylchloride→(6R,7R)-7-[[(2Z)-2-[2-[(tert-Butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacidN-(propan-2-yl)propan-2-amine→Iodomethylpivalate→Boc-cefcapenepivoxil
Cefcamate Pivoxil HydrochlorideOptimised routesteps: 6total yield: 65-70g(Cefcamate Pivoxil Hydrochloride (API))
(6R,7R)-7-Amino-3-(hydroxymethyl)-3-cephem-4-carboxylicacid→Trimethylsilyl(6R,7R)-7-amino-8-oxo-3-[[(trimethylsilyl)oxy]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→2-[2(Z)-2-Boc-amino-1,3-thiazol-4-yl]pent-2-enoicacid→Trimethylsilyl(6R,7R)-7-[[2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-8-oxo-3-[[(trimethylsilyl)oxy]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→Chlorosulfonicacidisocyanate→Sodium(6R,7R)-7-[[(2Z)-2-[2-[(tert-butoxycarbonyl)amino]-1,3-thiazol-4-yl]pent-2-enoyl]amino]-3-[(carbamoyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate→Iodomethylpivalate→Chloromethylpivalate→Boc-cefcapenepivoxil
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