Trifluoroacetic acid → 4-((R)-2-Amino-3-fluoro-propionyl)piperazine-1-carboxylic acid butyl ester

HRID 1185531Notes

Reaction equation

HRID 1185531 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:26])[C@@H:15]([NH:18]C(OC(C)(C)C)=O)[CH2:16][F:17])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4].C(O)(C(F)(F)F)=O>ClCCl>[CH2:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:26])[C@@H:15]([NH2:18])[CH2:16][F:17])[CH2:12][CH2:13]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 685998364-((R)-2-tert-Butoxycarbonylamino-3-fluoro-propionyl)-piperazine-1-carboxylic acid butyl ester

Product 1

HCID 685981694-((R)-2-Amino-3-fluoro-propionyl)piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 230 mg 4-((R)-2-tert-Butoxycarbonylamino-3-fluoro-propionyl)-piperazine-1-carboxylic acid butyl ester in 5 ml dichloromethane was added 1.0 ml TFA. After 12 h stirring at RT the solvents were removed and the residue was codistilled twice with toluene. Yield: 307 mg.

Workup

  1. customwere removed

Sources & evidence

ORD record
ord-dbbb33716249492ea3bef49b8e3a8ee8
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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