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

HRID 489816Notes

Reaction equation

HRID 489816 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[C:20]([F:23])([F:22])[F:21])=[O:5])C.[OH-].[Na+].Cl>CO>[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]([C:20]([F:22])([F:23])[F:21])[N:8]=1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21911370Ethyl-2-tert-butoxycarbonyloxyamino-4-trifluoromethyl-thiazole-5-carboxylate

Product 1

HCID 219113032-Tert-butoxycarbonyloxyamino-4-trifluoromethyl-thiazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of ethyl-2-tert-butoxycarbonyloxyamino-4-trifluoromethyl-thiazole-5-carboxylate (6.5 g, 19.1 mmol) in methanol (100 mL) was treated with a 1N aq. NaOH solution (573 mL). The mixture was stirred at rt overnight. The solution was cooled to 0° C. and acidified with a 6 M aq. HCl solution to pH 1 and extracted with chloroform (150 mL, 6×). The chloroform extracts were combined, dried (Na2SO4), filtered and concentrated under reduced pressure and in vacuo to obtain the title acid (5.75 g, 96%) as a white solid.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. extractionextracted with chloroform (150 mL, 6×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure and in vacuo
  6. customto obtain the title acid (5.75 g, 96%) as a white solid

Sources & evidence

ORD record
ord-29071f7156434766a39f8b7e53b6fa6f
Source dataset
uspto-grants-2005_12
Patent number
US06979694B2

Reaction notes

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