Trifluoroacetic acid → EtOAc EtOH H2O NH4OH

HRID 583695Notes

Reaction equation

HRID 583695 reaction equation
[C:1]([O:5][C:6](=[O:37])[C@@H:7]([NH:27][S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH2:8][NH:9][C:10](=[O:26])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][NH:20][C:21]2[S:22][CH:23]=[CH:24][N:25]=2)=[CH:13][CH:12]=1)(C)(C)[CH3:2].[C:38](O)([C:40](F)(F)F)=[O:39]>C(Cl)Cl>[CH3:2][CH2:1][O:5][C:6]([CH3:7])=[O:37].[CH3:40][CH2:38][OH:39].[NH4+:9].[OH-:5].[OH2:5].[S:22]1[CH:23]=[CH:24][N:25]=[C:21]1[NH:20][CH2:19][CH2:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]([NH:9][CH2:8][C@H:7]([NH:27][S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])[C:6]([OH:37])=[O:5])=[O:26])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867524504-[2-(Thiazol-2-ylamino)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester

Product 2

HCID 86752451EtOAc EtOH H2O NH4OHHCID 867524524-[2-(Thiazol-2-ylamino)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ester 24-6 (197 mg, 0.36 mmol) was dissolved in 1.8 mL CH2Cl2 and treated with 1.8 mL TFA. Once the starting material had disappeared, the reaction was concentrated, and flash chromatography (silica, 18:10:1:1 EtOAc/EtOH/NH4OH/H2O) provided 24-7 as a white solid. Rf 0.26 (silica, 18:10:1:1 EtOAc/EtOH/NH4OH/H2O).

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-be84b9d55e0c4e2d83430b4da88213f6
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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