Lithium Hydroxide → HCID 22457717, compound

HRID 2184745Notes

Reaction equation

HRID 2184745 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:10][CH2:11][CH2:12][S:13][CH2:14][CH:15]([C:22](=[O:29])[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:16][C:17]([O:19]CC)=[O:18])=[O:9])=[CH:4][CH:3]=1.[OH-].[Li+]>C(O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:10][CH2:11][CH2:12][S:13][CH2:14][CH:15]([C:22](=[O:29])[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)[CH2:16][C:17]([OH:19])=[O:18])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 22457730HCID 22457730, compound

Product 1

HCID 22457717HCID 22457717, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A solution of ethyl 3-({2-[(4-fluorophenyl)carbonylamino]ethylthio}methyl)-4-oxo-4-(3-pyridyl)butanoate (100 mg) and lithium hydroxide (1 eq) was stirred a temperature in ethanol-water (1:1, 2 mL) till the starting material disappeared. The solution was acidified and purified on preparative HPLC (C-18 prep column, 10% to 90% acetonitrile in water both containing 0.1% TFA) to give 91 mg of 3-({2-[(4-fluorophenyl)carbonylamino]ethylthio}methyl)-4-oxo-4-(3-pyridyl)butanoic acid. The acid (91 mg) was treated with ethyl chloroformate (1.1 eq) and triethylamine (1.1 eq) in tetrahydrofuran (2.5 mL) at room temperature for 10 minutes. Piperidine (1.1 eq) was added to the reaction mixture and stirred at room temperature overnight. The solution was concentrated and purified on preparative HPLC (C-18 prep column, 10% to 90% acetonitrile in water both containing 0.1% TFA) to give 66 mg of the title compound; ESMS (M+1)+458.

Workup

  1. custompurified on preparative HPLC (C-18 prep column, 10% to 90% acetonitrile in water both containing 0.1% TFA)

Sources & evidence

ORD record
ord-f3bc2d2ddd2c43bfbda86aa921b4856e
Source dataset
uspto-grants-2002_06
Patent number
US06399606B1

Reaction notes

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