Sodium Hydroxide → Sodium 3-((5-oxo-1-{3-((N-phenylcarbamoyl)amino)phenyl}pyrrolidin-3-yl)carbonylamino)-3-(3-pyridyl)propanoate

HRID 22889Notes

Reaction equation

HRID 22889 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14](=[O:22])[NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:8]=2)[CH2:5][CH:4]([C:23]([NH:25][CH:26]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)[CH2:27][C:28]([O:30]CC)=[O:29])=[O:24])[CH2:3]1.[OH-].[Na+:40]>C1COCC1>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14](=[O:22])[NH:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:8]=2)[CH2:5][CH:4]([C:23]([NH:25][CH:26]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)[CH2:27][C:28]([O-:30])=[O:29])=[O:24])[CH2:3]1.[Na+:40]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12135081ethyl 3-((5-oxo-1-{3-((N-phenylcarbamoyl) amino)phenyl}pyrrolidin-3-yl)carbonylamino)-3-(3-pyridyl)propanoate

Product 1

HCID 23675366Sodium 3-((5-oxo-1-{3-((N-phenylcarbamoyl)amino)phenyl}pyrrolidin-3-yl)carbonylamino)-3-(3-pyridyl)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-((5-oxo-1-{3-((N-phenylcarbamoyl)amino)phenyl}pyrrolidin-3-yl)carbonylamino)-3-(3-pyridyl)propanoate (75 mg, 0.14 mmol, 1.0 eq), THF (1.0 mL), and 1.0 N NaOH (0.15 mL, 1.1 eq) was stirred at room temperature overnight. The solvent was removed on rotary evaporator. The title compound was obtained as an off-white solid. 1H NMR (MeOH-d4, 400 MHz): δ 2.77 (m, 4), 3.30 (m, 1, overlap with solvent), 4.08 (m, 2), 5.35 (m, 1), 7.01(m, 2), 7.28 (m, 4), 7.41(m, 3), 7.66 (m, 1), 7.86 (m, 1), 8.39 (m, 1), 8.57 (m, 1). MS (ES+): 488 (M+H)+; (ES−): 486 (M−H)−.

Workup

  1. customThe solvent was removed on rotary evaporator

Sources & evidence

ORD record
ord-9ebbe4cbb1d443fa8387c62c8221f0ba
Source dataset
uspto-grants-2005_02
Patent number
US06849639B2

Reaction notes

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