Sodium Hydroxide → HCID 10276607, compound

HRID 1935250Notes

Reaction equation

HRID 1935250 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:35])[CH:12]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:6][CH:5]=1.[OH-].[Na+]>CO>[CH:14]1([CH2:13][CH:12]([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:36])=[O:2])=[CH:5][N:6]=2)=[O:35])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67483603HCID 67483603, compound

Product 1

HCID 10276607HCID 10276607, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 6-[3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionylamino]-nicotinic acid methyl ester (prepared in Example 25B-a, 45 mg, 0.094 mmol) in methanol (500 μL) was treated with a 1N aqueous sodium hydroxide solution (188 μL, 0.188 mmol). The reaction mixture was heated under reflux for 1 h and then allowed to cool to 25° C. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 15/1 methylene chloride/methanol) afforded 6-[3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionylamino]-nicotinic acid (15 mg, 34%) as a pale yellow solid: mp 155-158° C.; FAB-HRMS m/e calcd for C30H28N2O3 (M+H)+ 465.2178, found 465.2169.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-7dd4da5bc5a5403888136345a5f0b3cf
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

Loading…