4-[2-(1-Benzylimidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine → Ethanol ammonium hydroxide water

HRID 583656Notes

Reaction equation

HRID 583656 reaction equation
C([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:39]=[CH:38][C:19]([C:20]([NH:22][CH2:23][C@H:24]([NH:28][S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:25]([OH:27])=[O:26])=[O:21])=[CH:18][CH:17]=2)[N:10]=[CH:9]1)C1C=CC=CC=1>[Pd].C(O)=O.CO>[CH2:14]([OH:15])[CH3:13].[NH4+:8].[OH-:15].[OH2:15].[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([NH:22][CH2:23][C@H:24]([NH:28][S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:25]([OH:27])=[O:26])=[O:21])=[CH:38][CH:39]=2)[N:10]=[CH:9]1

Participants

5

Reactant 1

HCID 158507224-[2-(1-Benzylimidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine

Product 2

HCID 86596525Ethanol ammonium hydroxide waterHCID 1785233984-[2-(Imidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent

Procedure

A mixture of 3-8 (94 mg, 0.17 mmol), 10% Pd/C (94 mg), and 4.4% formic acid/CH3OH was stirred at ambient temperature under a hydrogen atmosphere (1 atm) for 72 h. The reaction mixture was filtered through a celite pad and the filtrate concentrated. Flash chromatography (silica, 5/3/0.5 CH2Cl2 /CH3OH/32% AcOH; then 10/1/1 ethanol/NH4OH/H2O) gave 3-9 as a colorless solid. Rf 0.33 (silica, 5/3/0.5 CH2Cl2 /CH3OH/32% AcOH).

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-eb64def831a643b1b082097476328dea
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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