L-Pyroglutamic Acid → HCID 14053691, compound

HRID 1029396Notes

Reaction equation

HRID 1029396 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=O.[C:10]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[C:10]([N:20]1[CH2:21][CH2:22][N:23]([C:7]([CH:2]2[NH:1][C:5](=[O:6])[CH2:4][CH2:3]2)=[O:9])[CH2:24][CH2:25]1)([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

Participants

5

Reactant 3

HCID 7405L-Pyroglutamic AcidHCID 10868DicyclohexylcarbodiimideHCID 643495Benzyl piperazine-1-carboxylate

Product 1

HCID 14053691HCID 14053691, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Pyroglutamic acid (112.4 g), 147.7 g of N-carbobenzoxypiperazine, 179.7 g of dicyclohexylcarbodiimide and 6.7 liters of acetonitrile were heated to reflux for 6 hours with stirring. The insoluble matters were removed by filtering the reaction mixture and the solvent was evaporated from the filtrate in vacuo. The residue was subjected to a silica gel column chromatography to give 190 g of oily N-carbobenzoxy-N'-(2-pyrrolidon-5-carbonyl)piperazine. Thirty grams of this was dissolved in 450 ml of methanol and the solution was subjected to a catalytic reduction using 3.0 g of 5% palladium-carbon with stirring at room temperature. The catalyst was removed by filtering the reaction solution and the solvent was evaporated in vacuo from the filtrate to give 20 g of the product. This was recrystallized from a mixture of methanol and ethyl acetate to give 17.5 g of desired compound, m.p. 162°-163° C.

Workup

  1. temperatureto reflux for 6 hours
  2. customThe insoluble matters were removed
  3. filtrationby filtering the reaction mixture
  4. customthe solvent was evaporated from the filtrate in vacuo

Sources & evidence

ORD record
ord-8ebb91f4d5d64a6eab0053ff85d67bb1
Source dataset
uspto-grants-1992_04
Patent number
US05102882

Reaction notes

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