Hydrochloric Acid → Diisopropylethylamine
Reaction equation
C=[C:2]1[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([N:20]([C:24]([NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:21][CH2:22][CH3:23])[CH2:16][CH2:15]2)[CH2:3]1.Cl.CC[O:37][CH2:38][CH3:39].[CH3:40]O>>[CH3:22][CH2:21][N:20]([CH:38]([CH3:39])[CH3:40])[CH:17]([CH3:18])[CH3:16].[CH2:27]([NH:26][C:24]([N:20]([CH:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH:4]2[CH:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:6][C:2](=[O:37])[CH2:3]2)[CH2:15][CH2:16]1)[CH2:21][CH2:22][CH3:23])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1Participants
6
Reactant 4
Product 2
Procedure
To a solution of 1-methylene-3-(SR)-((4-(N-(benzylaminocarbonyl)-N-(prop-1-yl)amino)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentane from Step D (1.8 g, 4.0 mmol) in methanol (50 mL) was added 1M hydrogen chloride in ether (6.0 mL, 6.0 mmol). The solution was cooled in a dry ice/acetone bath and ozone was bubbled into the solution until the blue color persisted. The excess ozone was removed with a stream of nitrogen and then dimethylsulfide (5 mL) was added. After 10 min, the bath was removed and the reaction was allowed to warm to rt over 16 h. The volatiles were removed in vacuo and the residue was purified by FC (ethyl acetate, then 1% DIPEA in ethyl acetate) to give the title compound (1.13 g).
Workup
- temperatureThe solution was cooled in a dry ice/acetone bath
- customozone was bubbled into the solution until the blue color
- customThe excess ozone was removed with a stream of nitrogen
- additiondimethylsulfide (5 mL) was added
- customthe bath was removed
- customThe volatiles were removed in vacuo
- customthe residue was purified by FC (ethyl acetate
Sources & evidence
- ORD record
- ord-7ee420401b6f40e196434632229fc3c2
- Source dataset
- uspto-grants-2002_10
- Patent number
- US06472410B1
Reaction notes
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