Trifluoroacetic acid → EtOAc EtOH H2O NH4OH

HRID 1599943Notes

Reaction equation

HRID 1599943 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-14d0a0d6e54d438a9a7602645e14dd01
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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