Trifluoroacetic acid → Trifluoroacetic acid

HRID 1527547Notes

Reaction equation

HRID 1527547 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:26])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:25])([F:24])[F:23])[CH:16]=1)=O)(C)(C)C.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]>C(Cl)Cl>[F:24][C:22]([F:23])([F:25])[O:21][C:17]1[CH:16]=[C:15]([NH:14][C:13]([C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:26])[CH:20]=[CH:19][CH:18]=1.[C:27]([OH:33])([C:29]([F:32])([F:31])[F:30])=[O:28]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 52716430HCID 52716430, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 28161015HCID 28161015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (8.52 g, 22.6 mmol) in CH2Cl2 (50 mL) was added TFA (8.65 mL, 113 mmol) and solution was stirred at RT for 12 h. The crude reaction mixture was concentrated under vacuum, Et2O was added and the white precipitate was filtered off to give the desired compound as a TFA salt. MS (LC/MS): 275.2 [M+H]+, 273.3 [M−H]−; tR (HPLC conditions a) 2.47 min.

Workup

  1. customThe crude reaction mixture
  2. concentrationwas concentrated under vacuum, Et2O
  3. additionwas added
  4. filtrationthe white precipitate was filtered off

Sources & evidence

ORD record
ord-549478e771474c478ed6420d252e0645
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

Loading…