Ethyl Acetate → HCID 86654951, compound

HRID 1615601Notes

Reaction equation

[C:1]([O:5][C:6](=[O:21])[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[C:19]#[N:20])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].C(OCC)(=O)C>C1COCC1.CN(C=O)C>[C:1]([O:5][C:6]([C:7]1[N:8]([C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[C:9]2[C:10]([C:19]=1[NH2:20])=[CH:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=2)=[O:21])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2-cyano-4-trifluoromethylphenylamino)acetic acid tert-butyl ester 5B (11.7 g, 39.0 mmol) in anhydrous THF (60 mL) and anhydrous DMF (60 mL) at 0° C. was added potassium tert-butoxide (8.74 g, 78.0 mmol). The reaction mixture was stirred at 0° C. for 5 minutes and benzyl chloroformate 5C (10 g, 58.7 mmol) was added. The reaction mixture was stirred at room temperature for 4 hours. Ethyl acetate (500 mL) was added and the organic layer was washed with water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by flash column chromatography to provide 3-amino-1-benzyloxycarbonyl-5-trifluoromethylindole-2-carboxylic acid tert-butyl ester 5D (5.96 g, 13.7 mmol).

Workup

stirringThe reaction mixture was stirred at room temperature for 4 hours
washthe organic layer was washed with water and brine
dry with materialThe organic layer was dried over sodium sulfate
customThe organic solvent was evaporated under reduced pressure
customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record: ord-55a414c7d5fd4b2d83182c4d76067077
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765757B2

Reaction notes

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