Benzyl carbamate → Ethyl 2-(benzyloxycarbonylamino)-3,3,3-trifluoro-2-hydroxypropanoate

HRID 58897

Reaction equation

HRID 58897 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12](=[O:22])([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:13]>ClCCl>[CH2:15]([O:14][C:12]([NH:13][C:3]([OH:9])([C:2]([F:10])([F:11])[F:1])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 12136Benzyl carbamateHCID 2737239Ethyl 3,3,3-trifluoro-2-oxopropanoate

Product 1

HCID 14377410Ethyl 2-(benzyloxycarbonylamino)-3,3,3-trifluoro-2-hydroxypropanoateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3,3,3-trifluoro-2-oxopropanoate (30 g, 176 mmol) in dichloromethane (1 L) was added benzyl carbamate (26.6 g). The reaction mixture was stirred at ambient temperature for 24 h and the resulting precipitate was collected by filtration and dried under vacuum to afford ethyl 2-(benzyloxycarbonylamino)-3,3,3-trifluoro-2-hydroxypropanoate (49.0 g, 87% yield), which was used directly without further purification.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-0013123ac2054632854381318601ebc4
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Linked notes

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