4-Nitro-3-phenyl-L-alanine → N-(2,6-Dichlorobenzoyl)-4-nitro-L-phenylalanine

HRID 16920

Reaction equation

HRID 16920 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:18]=1[C:19](Cl)=[O:20].[OH-].[Na+]>CC(C)=O>[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:18]=1[C:19]([NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)=[O:20]

Participants

5

Reactant 3

HCID 137064-Nitro-3-phenyl-L-alanineHCID 14798Sodium HydroxideHCID 783922,6-Dichlorobenzoyl chloride

Product 1

HCID 58018322N-(2,6-Dichlorobenzoyl)-4-nitro-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Concretely, 4-nitro-L-phenylalanine and 2,6-dichlorobenzoylchloride are condensed in a mixed solvent of a sodium hydroxide aqueous solution and acetone with keeping the reaction temperature at 5 to 15° C., and then crystallization is conducted to obtain a corresponding condensed substance, Nα-(2,6-dichlorobenzoyl)-4-nitro-L-phenylalanine almost quantitatively.

Workup

  1. customat 5 to 15° C.
  2. customcrystallization

Sources & evidence

ORD record
ord-fa9291b9544d4ee1a39d7a61a3b0ea03
Source dataset
uspto-grants-2010_06
Patent number
US07737274B2

Linked notes

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