Hydrochloric Acid → 3-Benzyloxy-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylic acid
Reaction equation
[CH2:1]([O:8][C:9]1[CH:36]=[CH:35][C:12]2[C:13]3[N:17]([CH2:18][CH2:19][O:20][C:11]=2[CH:10]=1)[C:16]1[CH:21]=[C:22]([C:25]([O:27]C)=[O:26])[CH:23]=[CH:24][C:15]=1[C:14]=3[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl.O>CO.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:36]=[CH:35][C:12]2[C:13]3[N:17]([CH2:18][CH2:19][O:20][C:11]=2[CH:10]=1)[C:16]1[CH:21]=[C:22]([C:25]([OH:27])=[O:26])[CH:23]=[CH:24][C:15]=1[C:14]=3[CH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of methyl 3-benzyloxy-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylate (173 mg, 0.36 mmol) in methanol (3.5 ml) and tetrahydrofuran (3.5 ml) was added 4N aqueous sodium hydroxide solution (1.7 ml), and the mixture was stirred for 13 hr. To the reaction mixture were added 2N hydrochloric acid (3.7 ml) and water, and the precipitated solid was collected by filtration and dried in vacuo. The obtained solid was purified by silica gel chromatography (hexane:ethyl acetate=1:1) to give 3-benzyloxy-12-cyclohexyl-6,7-dihydro-5-oxa-7a-azadibenzo[a,e]azulene-9-carboxylic acid (81 mg, yield 48%).
Workup
- filtrationthe precipitated solid was collected by filtration
- customdried in vacuo
- customThe obtained solid was purified by silica gel chromatography (hexane:ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-7f8be447bdbb4339a2fb158f0a8c6be6
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977331B1
Reaction notes
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