Trifluoroacetic acid → (2S)-2-((3S)-3-{(2-Amino-2-oxoethyl)[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid

HRID 349514Notes

Reaction equation

HRID 349514 reaction equation
[NH2:1][C:2](=[O:34])[CH2:3][N:4]([S:20]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([Cl:33])[CH:29]=2)[CH:24]=1)(=[O:22])=[O:21])[C@H:5]1[CH2:9][CH2:8][N:7]([C@@H:10]([CH3:18])[C:11]([O:13]C(C)(C)C)=[O:12])[C:6]1=[O:19].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2](=[O:34])[CH2:3][N:4]([S:20]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([Cl:33])[CH:29]=2)[CH:24]=1)(=[O:22])=[O:21])[C@H:5]1[CH2:9][CH2:8][N:7]([C@@H:10]([CH3:18])[C:11]([OH:13])=[O:12])[C:6]1=[O:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69223739tert-Butyl (2S)-2-((3S)-3-{(2-amino-2-oxoethyl)[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate

Product 1

HCID 69060748(2S)-2-((3S)-3-{(2-Amino-2-oxoethyl)[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acidYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2S)-2-((3S)-3-{(2-amino-2-oxoethyl)[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoate (1.4 g) was dissolved in DCM (35 ml), and trifluoroacetic acid (35 ml) was added. The mixture was stirred at room temperature for 2 h and then evaporated under reduced pressure. The residue was azeotroped with anhydrous dichloromethane and then dried under high vacuum. The residual viscous oil was triturated with diethyl ether to give the title compound (1.23 g) as a white solid.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was azeotroped with anhydrous dichloromethane
  3. customdried under high vacuum
  4. customThe residual viscous oil was triturated with diethyl ether

Sources & evidence

ORD record
ord-0d6eb395d6044eddb89d3fb11022107b
Source dataset
uspto-grants-2007_02
Patent number
US07179835B2

Reaction notes

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