Hydrochloric Acid → 2-Tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylic acid

HRID 9088

Reaction equation

C([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][O:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:8][C:7]=1[CH3:20])=[O:5])C.[OH-].[K+].Cl>O1CCCC1CCO>[C:16]([O:15][C:13]([O:12][NH:11][C:9]1[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:20])[N:8]=1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 55 °C

Procedure

A stirred solution of ethyl-2-tert-butoxycarbonyloxyamino-4-methyl-thiazole-5-carboxylate (10 g, 34.95 mmol) in tetrahydrofuran-ethanol (250 mL, 2:3) was treated with a 6N KOH solution (250 mL). The mixture was heated to 55° C. overnight. The solution was cooled to 0° C. and acidified with concd. HCl to pH 1. The solvent was evaporated in vacuo. The residue was washed with water, diethyl ether, dried in vacuo over anhydrous phosphorous pentoxide to obtain the title acid (6 g, 89%) as a white solid.

Workup

temperatureThe solution was cooled to 0° C.
customThe solvent was evaporated in vacuo
washThe residue was washed with water, diethyl ether
dry with materialdried in vacuo over anhydrous phosphorous pentoxide
customto obtain the title acid (6 g, 89%) as a white solid

Sources & evidence

ORD record: ord-8e2c9bc4dca442bda6037a7be6b1f8b6
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091223B2

Linked notes

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