Hydrochloric Acid → HCID 22467519, compound

HRID 1934652Notes

Reaction equation

C[O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:13]=2[C:14]([NH:16][CH2:17][C:18]2[CH:26]=[CH:25][C:21]3[O:22][CH2:23][O:24][C:20]=3[CH:19]=2)=[O:15])[CH2:7][CH2:6]1)=[O:4].CO.[OH-].[Na+].Cl>O1CCCC1>[C:3]([CH:5]1[CH2:6][CH2:7][CH:8]([NH:11][C:12]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][C:13]=2[C:14]([NH:16][CH2:17][C:18]2[CH:26]=[CH:25][C:21]3[O:22][CH2:23][O:24][C:20]=3[CH:19]=2)=[O:15])[CH2:9][CH2:10]1)([OH:4])=[O:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-[4-(methoxycarbonyl)cyclohexylamino]-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide (269 mg), methanol (10 mL), tetrahydrofuran (10 mL) and 1N-sodium hydroxide solution (5 mL) was stirred for an hour at 60° C. The mixture was acidified with 1N-hydrochloric acid to pH 4 and the organic solvent was removed by evaporation. The aqueous layer was diluted with water and extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 2-(4-carboxycyclohexylamino)-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide as yellow powders (253 mg).

Workup

customthe organic solvent was removed by evaporation
additionThe aqueous layer was diluted with water
extractionextracted with chloroform
washThe extract was washed with brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record: ord-4ff6b4837f834898a926d975bebeecfc
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384080B1

Reaction notes

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