Methanol → HCID 178522767, compound

HRID 1934667Notes

Reaction equation

C([O:9][C@@H:10]1[CH2:15][CH2:14][C@H:13]([NH:16][C:17]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:18]=2[C:19]([NH:21][CH2:22][C:23]2[CH:31]=[CH:30][C:26]3[O:27][CH2:28][O:29][C:25]=3[CH:24]=2)=[O:20])[CH2:12][CH2:11]1)(=O)C1C=CC=CC=1.CO.[OH-].[Na+]>O1CCCC1>[OH:9][C@@H:10]1[CH2:15][CH2:14][C@H:13]([NH:16][C:17]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:18]=2[C:19]([NH:21][CH2:22][C:23]2[CH:31]=[CH:30][C:26]3[O:27][CH2:28][O:29][C:25]=3[CH:24]=2)=[O:20])[CH2:12][CH2:11]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-(cis4-benzoyloxycyclohexylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (64.0 mg), methanol (5 mL), tetrahydrofuran (5 mL) and 1N-sodium hydroxide solution (1 mL) was stirred for 2 hours at 60° C. After evaporation of the organic solvent, the aqueous layer was diluted with water and extracted with ethyl acetate. The extract was washed with an aqueous saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 2-(cis-4-hydroxycyclohexylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide as yellow powders (50.5 mg).

Workup

customAfter evaporation of the organic solvent
additionthe aqueous layer was diluted with water
extractionextracted with ethyl acetate
washThe extract was washed with an aqueous saturated sodium bicarbonate solution, water and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record: ord-507bb508f2e64f8e8803a8b22c375eb3
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384080B1

Reaction notes

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