Benzoyl chloride → N-Benzoyl-L-valylglycine

HRID 330619Notes

Reaction equation

HRID 330619 reaction equation
[NH2:1][C@H:2]([C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+].[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[C:15]([NH:1][C@H:2]([C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide2×HCID 6993111Glycine, N-DL-valyl-

Product 1

HCID 53780318N-Benzoyl-L-valylglycine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of L-valyl-glycine (1.0 g. 5.74 mmol) in 1 N NaOH (4.74 ml, 5.74 mmol) cooled to -5° C., 6.89 ml (689 mmol) of 1N NaOH and 968 1 (6.89 mmol) of benzoyl chloride were alternately stirred in for 30 minutes. After 90 minutes, the reaction mixture was diluted with water and washed with diethyl ether. The product was isolated by precipitation in the aqueous layer which was acidified to pH 1.5. The precipitate was then washed with diluted HCl, water, and ether. Recrystallization from water afforded 1.16 g (73% overall yield from 1): mp 190°-191° C.; Rf(D)=0.2.

Workup

  1. washwashed with diethyl ether
  2. customThe product was isolated by precipitation in the aqueous layer which
  3. washThe precipitate was then washed with diluted HCl, water, and ether
  4. customRecrystallization from water
  5. customafforded
  6. custom1.16 g (73% overall yield from 1)

Sources & evidence

ORD record
ord-6826539a63fd494088bfc8c44cd257eb
Source dataset
uspto-grants-1990_01
Patent number
US04897444

Reaction notes

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