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

HRID 880213Notes

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-cc192331271d46448e91b52014d5eea5
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993567B2

Reaction notes

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