Trifluoroacetic acid → HCID 53880136, compound

HRID 1442949Notes

Reaction equation

HRID 1442949 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:21]([O:23]C(C)(C)C)=[O:22])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH3:8].[CH2:14]([S:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([C:21]([OH:23])=[O:22])[CH2:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68539988HCID 68539988, compound

Product 2

HCID 222AmmoniaYield 10%HCID 53880136HCID 53880136, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-4-Benzylsulfanyl-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester (Preparation 2, 130 mg, 3.3 mmol) in dichloromethane (2.5 ml) was added trifluoroacetic acid (2.5 ml) and the mixture stirred at room temperature under a nitrogen atmosphere for 36 hours. The solvent was removed under reduced pressure and the residue purified by ion-exchange chromatography using Dowex™ 50WX8-200 resin eluting first with water and then with 10% aq ammonia to give the title compound (66 mg, 75%) as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue purified by ion-exchange chromatography
  3. washeluting first with water

Sources & evidence

ORD record
ord-446e7a46af9c49cda5525f92880d3432
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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