Acetic Acid → HCID 54464964, compound

HRID 1590187Notes

Reaction equation

[CH2:1]1[C@@H:9]2[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][N:2]1[C:10]([CH2:12][CH:13]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[C:14]([OH:16])=[O:15])=[O:11].[N+](=[CH2:27])=[N-].C(O)(=O)C>C(OCC)C>[CH2:1]1[C@@H:9]2[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][N:2]1[C:10]([CH2:12][CH:13]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1)[C:14]([O:16][CH3:27])=[O:15])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 3-(cis-hexahydro-2-isoindolinylcarbonyl)-2-(4-methylbenzyl)propionic acid (100 mg) in diethyl ether (10 ml) was added a solution of diazomethane in diethyl ether (10 ml) with stirring at 0° C. After the mixture was stirred at room temperature for 1 hour, excess diazomethane was decomposed with acetic acid. The reaction mixture was washed successively with saturated sodium bicarbonate solution and brine and dried over MgSO4. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (4/1) to give 60 mg of methyl 3-(cis-hexahydro-2-isoindolinylcarbonyl)-2-(4-methylbenzyl)propionate as a colorless viscous oil.

Workup

stirringAfter the mixture was stirred at room temperature for 1 hour
washThe reaction mixture was washed successively with saturated sodium bicarbonate solution and brine
dry with materialdried over MgSO4
customAfter the solvent was evaporated under reduced pressure
customthe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (4/1)

Sources & evidence

ORD record: ord-dbb9d354fa414d4abff8333ed368fb6c
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05202335

Reaction notes

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