Trifluoroacetic acid → 4-[2-(1-Benzylimidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine

HRID 583655Notes

Reaction equation

HRID 583655 reaction equation
[C:1]([O:5][C:6](=[O:43])[C@@H:7]([NH:33][S:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:36])=[O:35])[CH2:8][NH:9][C:10](=[O:32])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[CH:22][N:23]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:24]=2)=[CH:13][CH:12]=1)(C)(C)[CH3:2].C(O)(C(F)(F)F)=[O:45]>C(Cl)Cl>[CH2:1]([OH:5])[CH3:2].[NH4+:9].[OH-:45].[OH2:5].[CH2:25]([N:23]1[CH:24]=[C:20]([CH2:19][CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]([C:10]([NH:9][CH2:8][C@H:7]([NH:33][S:34]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)(=[O:36])=[O:35])[C:6]([OH:43])=[O:5])=[O:32])=[CH:16][CH:15]=2)[N:21]=[CH:22]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 158507214-[2-(1-Benzyl-imidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester

Product 2

HCID 158507224-[2-(1-Benzylimidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanineHCID 86596525Ethanol ammonium hydroxide water

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-7 (252 mg, 0.42 mmol), TFA (3 mL) and CH2Cl2 (10 mL) was stirred at ambient temperature for 3 h, followed by concentration. Flash chromatography (silica, 9:0.5:0.5 ethanol/NH4OH/H2O (2×)) gave 3-8 as a viscous gum. Rf 0.08 (silica, 9:0.5:0.5 ethanol/NH4OH/H2O).

Workup

  1. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-4729f0b7fa9042f0b5efb77fde81fe69
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

Loading…