Trifluoroacetic acid → HCID 86585066, compound

HRID 1264412Notes

Reaction equation

HRID 1264412 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([S:13][C:14](=[O:16])[CH3:15])[CH2:10][C@H:9]1[C:17](=[O:35])[N:18]([CH2:20][C:21](=[O:34])[N:22]([C:24]1[CH:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=1)[CH3:23])[CH3:19])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:33][O:32][C:30](=[O:31])[C:27]1[CH:28]=[CH:29][C:24]([N:22]([C:21](=[O:34])[CH2:20][N:18]([C:17]([C@@H:9]2[CH2:10][C@@H:11]([S:13][C:14](=[O:16])[CH3:15])[CH2:12][NH:8]2)=[O:35])[CH3:19])[CH3:23])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86585067HCID 86585067, compound

Product 1

HCID 86585066HCID 86585066, compoundYield 116.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.92 g (5.7 mmol) (2S,4R)-4-Acetylsulfanyl-2-[[[(4-methoxycarbonyl-phenyl)-methyl-carbamoyl]-methyl]-methyl-carbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester in 60 ml CH2Cl2 were treated with 15 ml TFA at 0° C. until no starting material could be detected. The solution was concentrated, dissolved in toluene and evaporated 3 times yielding 2.7 g (93%) (2S,4R)-4-[[[(4-Acetylsulfanyl-pyrrolidine-2-carbonyl)-methyl-amino]-acetyl]-methyl-amino]-benzoic acid methyl ester.trifluoro-acetate salt as brown foam, MS 408 (MH+).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in toluene
  3. customevaporated 3 times

Sources & evidence

ORD record
ord-e60e8c8a92db4068bc51aee28b706cfa
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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