Sodium hydride → benzyl N-(3,4-dimethoxybenzoyl)-(L)-pyroglutamate

HRID 543256Notes

Reaction equation

HRID 543256 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[H-].[Na+].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[C:24](Cl)=[O:25]>C1C=CC=CC=1>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[O:30][CH3:31])[C:24]([N:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77070Veratroyl chlorideHCID 2381219Benzyl 5-oxoprolinate

Product 1

HCID 13655570benzyl N-(3,4-dimethoxybenzoyl)-(L)-pyroglutamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A solution of 24.1 g (0.11 mol) of benzyl (L)-pyroglutamate, prepared according to Example II(1), in 200 ml of benzene is added over 11/2 hours to a suspension of 5.28 g (0.11 mol) of sodium hydride in 20 ml of dry benzene. After stirring for 1 hour at ordinary temperature, a solution of 22.1 g (0.11 mol) of 3,4-dimethoxybenzoyl chloride in 180 ml of benzene is run in.

Workup

  1. additionis added over 11/2 hours

Sources & evidence

ORD record
ord-c8661d09bb9343e4b63c5521de3f94bf
Source dataset
uspto-grants-1987_04
Patent number
US04661512

Reaction notes

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