Trifluoroacetic acid → HCID 22490234, compound

HRID 2179924Notes

Reaction equation

HRID 2179924 reaction equation
C([O:5][C:6](=[O:40])[CH:7]([N:15]([C:30](=[O:39])[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[Cl:38])[CH2:16][C:17]1[S:18][CH:19]=[CH:20][C:21]=1[C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=1)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:38][C:32]1[CH:33]=[C:34]([Cl:37])[CH:35]=[CH:36][C:31]=1[C:30]([N:15]([CH2:16][C:17]1[S:18][CH:19]=[CH:20][C:21]=1[C:22]1[CH:23]=[C:24]([F:29])[CH:25]=[C:26]([F:28])[CH:27]=1)[CH:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:6]([OH:40])=[O:5])=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20779310HCID 20779310, compound

Product 1

HCID 22490234HCID 22490234, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-{(2,4-Dichloro-benzoyl)-[3-(3,5-difluoro-phenyl)-thiophen-2-ylmethyl]-amino}-3-phenyl-propionic acid tert-butyl ester (37.63 mg, 0.0625 mmol.) in dichloromethane (1 ml.), was added trifluoroacetic acid (1 ml.). The reaction mixture was stirred at room temperature during 1 hr. TLC monitored the progress of the reaction. When the reaction was completed, the mixture was concentrated under reduced pressure on a rotary evaporator, followed by silica chromatography using 90% ethylacetate, 10% methanol and 1 drop of acetic acid, afforded 2-{(2,4-Dichloro-benzoyl)-[3-(3,5-difluoro-phenyl)-thiophen-2-ylmethyl]-amino}-3-phenyl-propionic acid in 85% yield. 1H NMR (Varian 400 MHz, CDCl3) δ(ppm), 7.22 (m, 8H, ArH), 7.00 (m, 2H, ArH), 6.82 (m, 2H, ArH), 6.50 (m, 1H, ArH), 4.95 (m, 0.5H, NCH2), 4.65 (m, 0.5H, NCH2), 4.10 (m, 1H, NCH2), 3.60 (m, 1H, CHCH2), 3.20 (m, 1H, CHCH2), 3.05 (m, 1H, CHCH2). MS, 546.00 found.

Workup

  1. customthe progress of the reaction
  2. concentrationthe mixture was concentrated under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-f4a619065d7c498599dfa8eb91a597fd
Source dataset
uspto-grants-2005_05
Patent number
US06887877B2

Reaction notes

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