Sodium Hydroxide → 3-({5-Oxo-1-(3-(1,3-thiazolin-2-ylamino)phenyl)pyrrolidin-3-yl}carbonylamino)-3-(3-pyridyl)propanoic acid

HRID 22890Notes

Reaction equation

HRID 22890 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]3[S:15][CH2:16][CH2:17][N:18]=3)[CH:8]=2)[CH2:5][CH:4]([C:19]([NH:21][CH:22]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH2:23][C:24]([O:26]CC)=[O:25])=[O:20])[CH2:3]1.[OH-].[Na+]>C1COCC1>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]3[S:15][CH2:16][CH2:17][N:18]=3)[CH:8]=2)[CH2:5][CH:4]([C:19]([NH:21][CH:22]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[CH2:23][C:24]([OH:26])=[O:25])=[O:20])[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12135084HCID 12135084, compound

Product 1

HCID 121350833-({5-Oxo-1-(3-(1,3-thiazolin-2-ylamino)phenyl)pyrrolidin-3-yl}carbonylamino)-3-(3-pyridyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-({5-oxo-1-(3-(1,3-thiazolin-2-ylamino)phenyl)pyrrolidin-3-yl}carbonylamino)-3-(3-pyridyl)propanoate (75 mg, 0.16 mmol, 1.0 eq), THF (1.0 mL), and 1.0 N NaOH (0.16 mL, 1.0 eq) was stirred at room temperature overnight. The solvent was removed on rotary evaporator. The title compound was abstained as an off-white solid from preparative HPLC. 1H NMR (MeOH-d4, 400 MHz): δ 2.68-2.99 (m, 4), 3.35 (m, 1), 3.67 (m, 2), 4.05 (m, 4), 5.42 (m, 1), 7.16 (m, 1), 7.52 (m, 2), 7.78 (m, 1), 7.88 (s, 1), 8.28 (m, 1), 8.62 (m, 1), 8.75 (m, 1). MS (ES+): 455 (M+H)+; (ES−): 453 (M−H)−.

Workup

  1. customThe solvent was removed on rotary evaporator

Sources & evidence

ORD record
ord-d62c06d28ab14131b1e0d2279a033602
Source dataset
uspto-grants-2005_02
Patent number
US06849639B2

Reaction notes

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