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

HRID 265897Notes

Reaction equation

HRID 265897 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:39]=[CH:38][C:19]([C:20]([N:22]([NH2:37])[CH2:23][C@H:24]([S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:25]([OH:27])=[O:26])=[O:21])=[CH:18][CH:17]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)=O.CO>[CH2:14]([OH:15])[CH3:13].[OH2:15].[NH4+:8].[OH-:15].[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:39]=[CH:38][C:19]([C:20]([N:22]([NH2:37])[CH2:23][C@H:24]([S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:29])=[O:30])[C:25]([OH:27])=[O:26])=[O:21])=[CH:18][CH:17]=2)[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 677209964-[2-(N-Benzylimidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonyl-amino-beta-alanine

Product 2

HCID 677209964-[2-(N-Benzylimidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonyl-amino-beta-alanineHCID 86596525Ethanol ammonium hydroxide water

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent

Procedure

A mixture of 25-7 (94 mg, 0.17 mmol), 10% Pd/C (94 mg), and 4% formic acid/CH3OH (50 mL) was stirred under a hydrogen atmosphere at ambient temperature for 4 days. Filtration, concentration of the filtrate, and the flash chromatography (silica, 10:1:1 ethanol/H2O/NH4OH) gave 25-7 as a solid. TLC Rf =0.31 (silica, 10:1:1 ethanol/NH4OH/H2O);

Workup

  1. filtrationFiltration, concentration of the filtrate

Sources & evidence

ORD record
ord-6e91b82776934849b5cf4cebab229be9
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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