HCID 86708076, compound → HCID 86708077, compound
Reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][C:25]([F:50])([F:49])[CH2:26][C@@H:27]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[N:28]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-])=O)=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH:29]([CH3:31])[CH3:30])=[O:21])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][C:25]([F:50])([F:49])[CH2:26][C@@H:27]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[N:28]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH:29]([CH3:30])[CH3:31])=[O:21])[CH:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:4]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To the material from Step 10 (81 mg, 0.113 mmol) and 10% palladium on carbon (11.99 mg, 0.011 mmol) was added ethyl acetate (1.3 mL). The reaction mixture was purged with nitrogen, and stirred under hydrogen (1 atm) overnight. Upon addition of DCM, the reaction mixture was filtered through celite, washed with dichloromethane, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel using ethyl acetate-hexanes (0:100 to 90:10) to afford 50 mg of the title compound as a colorless foam. LCMS (M+1)=689.
Workup
- customThe reaction mixture was purged with nitrogen
- additionUpon addition of DCM
- filtrationthe reaction mixture was filtered through celite
- washwashed with dichloromethane
- concentrationthe filtrate was concentrated in vacuo
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-d30f5ada331246148ca0e25f0ef9acc8
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079834B2
Reaction notes
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