Lithium Hydroxide → 4-[2-(Indol-2-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine

HRID 583661Notes

Reaction equation

HRID 583661 reaction equation
C[O:2][C:3](=[O:37])[C@@H:4]([NH:27][S:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH2:5][NH:6][C:7](=[O:26])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][C:17]2[NH:18][C:19]3[C:24]([CH:25]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:10][CH:9]=1.[Li+].[OH-]>C1COCC1>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[C:17]1[CH2:16][CH2:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]([NH:6][CH2:5][C@H:4]([NH:27][S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:29])=[O:30])[C:3]([OH:37])=[O:2])=[O:26])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 158507244-[2-(Indol-2-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine methyl ester

Product 1

HCID 158507254-[2-(Indol-2-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ester 4-5 (147 mg, 0.28 mmol), and 1N LiOH (0.70 mL, 0.70 mmol), were, combined in 3 mL THF. After 16 h the mixture was concentrated and purified by flash chromatography (silica, 33:20:1:1 EtOAc/EtOH/NH4OH/H2O) providing 4-6 as a white solid. Rf 0.33 (silica, 33:20:1:1 EtOAc/EtOH/NH4OH/H2O).

Workup

  1. concentrationAfter 16 h the mixture was concentrated
  2. custompurified by flash chromatography (silica, 33:20:1:1 EtOAc/EtOH/NH4OH/H2O)

Sources & evidence

ORD record
ord-d3acf0d7904743fdbe3c94c140069ff9
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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