5-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl ester → Ethyl-2-tert-butoxycarbonyloxyamino-4-trifluoromethyl-thiazole-5-carboxylate

HRID 9090

Reaction equation

HRID 9090 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].[C:16]([O:20][C:21]([O:23]C(OC(C)(C)C)=O)=[O:22])([CH3:19])([CH3:18])[CH3:17]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][O:23][C:21]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:22])=[N:8][C:7]=1[C:12]([F:14])([F:15])[F:13])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 676565-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl esterHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 21911370Ethyl-2-tert-butoxycarbonyloxyamino-4-trifluoromethyl-thiazole-5-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of ethyl-2-amino-4-trifluoromethyl-thiazole-5-carboxylate (5.05 g, 21.02 mmol), di-t-butyldicarbonate (4.82 g, 22.07 mmol) and 4-dimethylaminopyridine (260 mg, 2.1 mmol) in dichloromethane (209 mL) was stirred under nitrogen for 1.5 h. The solvent was evaporated in vacuo. The residue was chromatographed on a silica gel column. Elution with 5% EtOAc in hexanes, followed by 15% EtOAc in hexanes afforded the title compound (6.57 g, 92%) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was chromatographed on a silica gel column
  3. washElution with 5% EtOAc in hexanes

Sources & evidence

ORD record
ord-1489de592ed543aead9b9b3cc9eda428
Source dataset
uspto-grants-2006_08
Patent number
US07091223B2

Linked notes

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