2-Naphthoyl chloride → 3-cyano-N-(2-naphthoyl)-L-alanine

HRID 267149

Reaction equation

HRID 267149 reaction equation
[C:1]([CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH2:5])#[N:2].[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:19](Cl)=[O:20]>[OH-].[Na+]>[C:1]([CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH:5][C:19]([C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=1)=[O:20])#[N:2]

Participants

4

Reactant 2

HCID 752462-Naphthoyl chlorideHCID 4397423-cyano-L-alanine

Product 1

HCID 538745083-cyano-N-(2-naphthoyl)-L-alanineYield 18.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.114 g of 3-cyano-L-alanine was dissolved in 5 ml of 1N sodium hydroxide solution and treated with 0.285 g of 2-naphthoyl chloride at 0° C. After acidification with 2M hydrochloric acid and flash chromatography on silica gel using 25% methanol in dichloromethane for the elution there was obtained 0.049 g of 3-cyano-N-(2-naphthoyl)-L-alanine of melting point 95°-100° C.

Workup

  1. washAfter acidification with 2M hydrochloric acid and flash chromatography on silica gel using 25% methanol in dichloromethane for the elution there

Sources & evidence

ORD record
ord-6b76bce827a842f5a4d4e820d568166d
Source dataset
uspto-grants-1997_07
Patent number
US05652369

Linked notes

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