Lithium Hydroxide → HCID 22315239, compound

HRID 430184Notes

Reaction equation

HRID 430184 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[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-].[Li+]>O1CCCC1>[CH:14]1([CH2:13][CH:12]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:30])=[O:2])=[CH:5][N:6]=2)=[O:29])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54426411HCID 54426411, compound

Product 1

HCID 22315239HCID 22315239, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 6-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionylamino]-nicotinic acid methyl ester (prepared in Example 53(B)(a), 100 mg, 0.23 mmol) in tetrahydrofuran (500 μL) was treated with a 0.8M aqueous lithium hydroxide solution (300 μL, 0.23 mmol). The solution was stirred at 25° C. for 4 h. The reaction mixture was then directly purified by column chromatography. Flash chromatography (Merck Silica gel 60, 230-400 mesh, ⅓ methanol/ethyl acetate) afforded 6-[3-cyclopentyl-2-(4-methanesulfonylphenyl)-propionylamino]-nicotinic acid (65 mg, 70%) as a white solid: mp 191-193° C.; FAB-HRMS m/e calcd for C21H24N2O5S (M+H)+ 417.1484, found 417.1484.

Workup

  1. customThe reaction mixture was then directly purified by column chromatography

Sources & evidence

ORD record
ord-7c10e9ea1b1f48dab64e3ba25db16e1e
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

Loading…