Benzoyl chloride → benzyl N-benzoyl-(L)-pyroglutamate

HRID 543255Notes

Reaction equation

HRID 543255 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:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>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:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 2381219Benzyl 5-oxoprolinate

Product 1

HCID 13655564benzyl N-benzoyl-(L)-pyroglutamateYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Conditions

Temperature
55 °C

Procedure

A solution of 21.9 g (0.1 mol) of benzyl (L)-pyroglutamate (prepared according to Example II(1)) in 150 ml of benzene is added over an hour to a suspension of 4.8 g (0.1 mol) of sodium hydride in 15 ml of dry benzene. The mixture is stirred for one hour at ordinary temperature and 14.1 g (0.1 mol) of benzoyl chloride diluted in benzene are then introduced. The reaction mixture is stirred for 4 hours at 55° C. and then for 18 hours at ordinary temperature. After the mixture has been washed with water, the solvent evaporated off and the residue taken up with ether, white crystals of melting point=101°/2° C. are obtained; yield=70%; Rf=0.68 (A).

Workup

  1. additionare then introduced
  2. waitfor 18 hours at ordinary temperature
  3. washAfter the mixture has been washed with water
  4. customthe solvent evaporated off
  5. customtaken up with ether, white crystals of melting point=101°/2° C.
  6. customare obtained

Sources & evidence

ORD record
ord-dade466880d54c7fa19f26a9a55fbb81
Source dataset
uspto-grants-1987_04
Patent number
US04661512

Reaction notes

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