2,4-bisbenzyloxy-N-butyl-5-(5-hydroxy-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamide → N-butyl-2,4-dihydroxy-5-(5-hydroxy-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamide

HRID 1927702Notes

Reaction equation

[H][H].C([O:10][C:11]1[CH:24]=[C:23]([O:25]CC2C=CC=CC=2)[C:22]([C:33]([N:35]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[C:40]([OH:44])[CH:41]=3)[CH2:36]2)=[O:34])=[CH:21][C:12]=1[C:13]([N:15]([CH2:17][CH2:18][CH2:19][CH3:20])[CH3:16])=[O:14])C1C=CC=CC=1>[Pd].C1COCC1>[CH2:17]([N:15]([CH3:16])[C:13](=[O:14])[C:12]1[CH:21]=[C:22]([C:33]([N:35]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[C:40]([OH:44])[CH:41]=3)[CH2:36]2)=[O:34])[C:23]([OH:25])=[CH:24][C:11]=1[OH:10])[CH2:18][CH2:19][CH3:20]

Participants

Conditions

Temperature: 22 °C

Procedure

10 ml of THF, 200 mg of 5% Pd/C (50.5% of H2O) and 15.884 ml (0.708 mmol) of hydrogen are added to 200 mg (0.354 mmol) of 2,4-bisbenzyloxy-N-butyl-5-(5-hydroxy-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamide in an autoclave, and the mixture is stirred for 20 h at 22° C. Filtration, subsequent evaporation and chromatography of the residue gives 75 mg (55.1%) of N-butyl-2,4-dihydroxy-5-(5-hydroxy-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamide “A1”);

Workup

filtrationFiltration, subsequent evaporation and chromatography of the residue

Sources & evidence

ORD record: ord-8a3c50852c65419db4dfd3b4717f837c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183279B2

Reaction notes

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