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

HRID 543257Notes

Reaction equation

HRID 543257 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]([CH2:29][C:30](Cl)=[O:31])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>C1C=CC=CC=1>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:29][C:30]([N:1]2[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]2[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])=[O:31])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2381219Benzyl 5-oxoprolinateHCID 3604458(3,4-Dimethoxyphenyl)acetyl chloride

Product 1

HCID 13655575benzyl N-(3,4-dimethoxyphenylacetyl)-(L)-pyroglutamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Conditions

Temperature
55 °C

Procedure

A solution of 17.5 g (80 mmol) of benzyl (L)-pyroglutamate, prepared according to Example II(1), in 150 ml of benzene is added over 1 hour to a suspension of 3.85 g (80 mmol) of sodium hydride in 15 ml of dry benzene. After stirring for 1 hour at ordinary temperature, a solution of 17.2 g (80 mmol) of 3,4-dimethoxyphenylacetyl chloride in 150 ml of benzene is run in. The mixture is heated at 55° C. for 6 hours and stirred at ordinary temperature for 15 hours, washed with 2×120 ml of water, dried and evaporated. The residue was purified by chromatography on a silica column using a chloroform/acetone mixture as the eluent. Thus gives 60% of a pure waxy product of Rf=0.46 (A).

Workup

  1. stirringstirred at ordinary temperature for 15 hours
  2. washwashed with 2×120 ml of water
  3. customdried
  4. customevaporated
  5. customThe residue was purified by chromatography on a silica column

Sources & evidence

ORD record
ord-fbd4c66a2c4e496c846e31bf6dbf190b
Source dataset
uspto-grants-1987_04
Patent number
US04661512

Reaction notes

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