Triethylamine → benzyl N-[2-ethylhexanoyl]-(L)-pyroglutamate

HRID 543253Notes

Reaction equation

HRID 543253 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].C(N(CC)CC)C.[CH2:24]([CH:26]([CH2:30][CH2:31][CH2:32][CH3:33])[C:27](Cl)=[O:28])[CH3:25]>C(Cl)(Cl)Cl>[CH2:24]([CH:26]([CH2:30][CH2:31][CH2:32][CH3:33])[C:27]([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:28])[CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 791032-Ethylhexanoyl chlorideHCID 2381219Benzyl 5-oxoprolinate

Product 1

HCID 13655558benzyl N-[2-ethylhexanoyl]-(L)-pyroglutamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

39.4 g (180 mmol) of benzyl (L)-pyroglutamate, prepared according to Example II(1), are dissolved in 160 ml of chloroform and 28.4 g (28 mmol) of triethylamine at ordinary temperature. A solution of 29.3 g (180 mmol) of 2-ethylhexanoyl chloride in 40 ml of chloroform is run in and the mixture is heated under reflux for 5 hours.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours

Sources & evidence

ORD record
ord-f480a0d847784f09859cad69f5e1b07d
Source dataset
uspto-grants-1987_04
Patent number
US04661512

Reaction notes

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