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

HRID 1048903Notes

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-8f88219630a54ffb8fbd898735d3f4ac
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382219B2

Reaction notes

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