1,4-Cyclohexadiene → L-Aspartyl 1-aminocyclopropanecarboxylic acid, 2,5-dimethylcyclopentyl ester

HRID 2231182Notes

Reaction equation

HRID 2231182 reaction equation
C([CH:8]([C:37](=[O:39])[OH:38])[C@@H:9]([C:21]([CH:23]1[CH2:25][C:24]1([NH2:36])[C:26]([O:28][CH:29]1[CH:33]([CH3:34])[CH2:32][CH2:31][CH:30]1[CH3:35])=[O:27])=[O:22])[NH:10]C(OCC1C=CC=CC=1)=O)C1C=CC=CC=1.C1CC=CCC=1>[Pd].C(O)C>[NH2:10][C@H:9]([C:21]([CH:23]1[CH2:25][C:24]1([NH2:36])[C:26]([O:28][CH:29]1[CH:33]([CH3:34])[CH2:32][CH2:31][CH:30]1[CH3:35])=[O:27])=[O:22])[CH2:8][C:37](=[O:38])[OH:39]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 86742388beta-Benzyl-N-benzyloxycarbonyl-L-aspartyl-1-aminocyclopropanecarboxylic acid, 2,5-dimethylcyclopentyl ester

Product 1

HCID 86742387L-Aspartyl 1-aminocyclopropanecarboxylic acid, 2,5-dimethylcyclopentyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of compound 3 (0.31 g), 1,4-cyclohexadiene (0.46 g), 10% palladium-on-carbon (0.3 g) and 95% ethanol (10 ml) was placed in an ultrasonic bath for 10 minutes. The mixture was then filtered through Celite, and the solvent was evaporated to yield 130 mg of a colorless oil which solidified upon standing. This was purified by HPLC using a reverse phase C18 column, 60% methanol in water as eluent to yield the desired product as a white solid (72 mg, 40%). MP: 155.5°-157° C.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c41ad7f919de428c84031c77b2463116
Source dataset
uspto-grants-1988_11
Patent number
US04781927

Reaction notes

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