2-Methoxyphenylacetic acid → (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-4-perhydroisoindolone

HRID 55426

Reaction equation

[OH:1][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:10]2[CH:6]([CH2:7][NH:8][CH2:9]2)[C:5](=[O:11])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][C:36](O)=[O:37].Cl.CN(C)CCCN=C=NCC>ClCCl.O.OC1C2N=NNC=2C=CC=1>[OH:1][C:2]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH:10]2[CH:6]([CH2:7][N:8]([C:36](=[O:37])[CH2:35][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[O:28][CH3:27])[CH2:9]2)[C:5](=[O:11])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 2.8 g of (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-4-perhydroisoindolone and 1.3 cm3 of triethylamine in 60 cm3 of anhydrous dichloromethane are added 1.55 g of (2-methoxyphenyl)acetic acid, 0.03 g of hydroxybenzotriazole hydrate and 1.96 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. After stirring for 20 hours at 20° C., the reaction mixture is washed with 100 cm3 of water, dried over magnesium sulphate and then concentrated to dryness under reduced pressure (2.7 kPa). The residue obtained is recrystallized in ethyl ether and the crystals are drained and then dried under reduced pressure (2.7 kPa). 3.1 g of (3aRS,7RS,7aSR)-7-hydroxy-7-(2-methoxyphenyl)-2-[(2-methoxyphenyl)acetyl]-4-perhydroisoindolone are obtained, in the form of a white solid melting at 184° C.

Workup

washthe reaction mixture is washed with 100 cm3 of water
dry with materialdried over magnesium sulphate
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customThe residue obtained
customis recrystallized in ethyl ether
customdried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-7e0c0a8a08d54cafae99d5a80f6fa36a
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05624950

Linked notes

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