Trifluoroacetic acid → 4-[2-(N-Benzylimidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonyl-amino-beta-alanine

HRID 1599909Notes

Reaction equation

HRID 1599909 reaction equation
[C:1]([O:5][C:6](=[O:43])[C@@H:7]([S:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:36])=[O:35])[CH2:8][N:9]([C:11](=[O:33])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][C:21]2[N:22]=[CH:23][N:24]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:25]=2)=[CH:14][CH:13]=1)[NH2:10])(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].[CH2:26]([N:24]1[CH:25]=[C:21]([CH2:20][CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:11]([N:9]([NH2:10])[CH2:8][C@H:7]([S:34]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)(=[O:35])=[O:36])[C:6]([OH:43])=[O:5])=[O:33])=[CH:13][CH:14]=2)[N:22]=[CH:23]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 677210604-[2-(1-Benzyl-imidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonyl-amino-beta-alanine tert-butyl ester

Product 2

HCID 677209964-[2-(N-Benzylimidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonyl-amino-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 (2x)) 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-01e95d5258ed483d93285d7c2437a1a2
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

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