Isopropanol → HCID 68044582, compound
Reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][CH:25]([F:46])[CH2:26][C@@H:27]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[NH:28][S:29]([C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)(=[O:31])=[O: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].[CH3:47][CH:48](O)[CH3:49].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][CH:25]([F:46])[CH2:26][C@@H:27]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[N:28]([S:29]([C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)(=[O:31])=[O:30])[CH:48]([CH3:49])[CH3:47])=[O:21])[CH:7]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]Participants
6
Procedure
To a solution of the material from Step 5 (50 mg, 0.076 mmol), 2-propanol (0.023 mL, 0.304 mmol) and Ph3P (80 mg, 0.304 mmol) in THF (1 mL) at 0° C. was slowly added diisopropyl azodicarboxylate (0.059 mL, 0.304 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated to dryness and the residue was purified by column chromatography on silica gel using ethyl acetate-hexanes (0:100 to 90:10) to afford 31 mg of the title compound as a colorless foam. LCMS (M+1)=701.
Workup
- customat 0° C.
- concentrationThe reaction mixture was concentrated to dryness
- customthe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-3898e4e8c3734ab6a228613d6a94a503
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079834B2
Reaction notes
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