Ethanol → HCID 21948278, compound
Reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH2:18]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31]([CH2:34][C:35]2(C(O)=O)[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH2:36]2)[C:30](=[O:51])[CH2:29]1)=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([N:54]([CH2:57]C)CC)C.C1(C)C=CC=CC=1.[CH2:66]([OH:68])[CH3:67]>>[C:44]([O:43][C:41]([N:38]1[CH2:39][CH2:40][C:35]([CH2:34][N:31]2[CH2:32][CH2:33][N:28]([C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:27])[CH2:29][C:30]2=[O:51])([NH:54][C:57]([O:68][CH2:66][CH3:67])=[O:8])[CH2:36][CH2:37]1)=[O:42])([CH3:47])([CH3:46])[CH3:45]Participants
6
Procedure
Diphenylphosphoryl azide (15.8 ml) was added to a mixture of 4-[[4-(benzyloxycarbonyl)-2-oxo-1-piperazinyl]methyl]-1-(tert-butoxycarbonyl)-4-piperidinecarboxylic acid (29 g) obtained in Reference Example 6, triethylamine (10.2 ml) and toluene (290 ml) at 0° C. under stirring, and the mixture was stirred at room temperature for 1 hour, and at 100° C. for 2 hours. Ethanol (290 ml) was added, and the mixture was heated under reflux for 12 hours, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=1/3-ethyl acetate/methanol=10/1) to obtain the title compound (26 g, 82%) as pale yellow powders.
Workup
- stirringthe mixture was stirred at room temperature for 1 hour
- temperaturethe mixture was heated
- temperatureunder reflux for 12 hours
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=1/3-ethyl acetate/methanol=10/1)
Sources & evidence
- ORD record
- ord-08afa4d7aef34e22a359390f36291752
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07109200B2
Reaction notes
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