Sodium hydride → benzyl N-hexanoyl-(L)-pyroglutamate

HRID 543254Notes

Reaction equation

HRID 543254 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+].[C:19](Cl)(=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1C=CC=CC=1>[C:19]([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])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67340Hexanoyl chlorideHCID 2381219Benzyl 5-oxoprolinate

Product 1

HCID 13655560benzyl N-hexanoyl-(L)-pyroglutamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Conditions

Temperature
50 °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 10.9 g (81 mmol) of hexanoyl chloride in 140 ml of benzene is run in. The mixture is heated at 50° C. for 5 hours and then stirred at ordinary temperature for 15 hours, washed with water (2×100 ml), dried and evaporated.

Workup

  1. stirringstirred at ordinary temperature for 15 hours
  2. washwashed with water (2×100 ml)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-6c5d3141a5544457b033ec563482f565
Source dataset
uspto-grants-1987_04
Patent number
US04661512

Reaction notes

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