CAS 153012-24-9

tert-Butyl[4-[(2Z)-1-oxo-1-[(methylsulfonyl)oxy]pent-2-en-2-yl]-1,3-thiazol-2-yl]carbamate

Codes: Cefcamate Pivoxil Hydrochloride-022

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)

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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

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