Triethylamine → benzyl N-dipropylacetyl-(L)-pyroglutamate

HRID 543252Notes

Reaction equation

HRID 543252 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:27]([CH2:31][CH2:32][CH3:33])[C:28](Cl)=[O:29])[CH2:25][CH3:26]>C(Cl)(Cl)Cl>[CH2:24]([CH:27]([CH2:31][CH2:32][CH3:33])[C:28]([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:29])[CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 762402-Propylvaleryl chlorideHCID 2381219Benzyl 5-oxoprolinate

Product 1

HCID 86741459benzyl N-dipropylacetyl-(L)-pyroglutamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

50.3 g (230 mmol) of benzyl (L)-pyroglutamate, prepared according to Example II(1), are dissolved in 200 ml of chloroform and 36.3 g (359 mmol) of triethylamine at ordinary temperature. A solution of 37.4 g (230 mmol) of dipropylacetyl chloride in 50 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-4e6e532a6c28496f8fdf3b4715dde935
Source dataset
uspto-grants-1987_04
Patent number
US04661512

Reaction notes

Loading…