Isobutanol → HCID 135430992, compound
Reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(O[C:14]1[C:19]([C:20]2[NH:21][C:22](=[O:36])[C:23]3[C:24](=[C:26]([CH2:33][CH2:34][CH3:35])[N:27]([CH2:29][CH2:30][O:31][CH3:32])[N:28]=3)[N:25]=2)=[CH:18][C:17]([S:37]([N:40]2[CH2:45][CH2:44][N:43]([CH2:46][CH3:47])[CH2:42][CH2:41]2)(=[O:39])=[O:38])=[CH:16][N:15]=1)C.[CH3:48][CH:49]([CH3:52])[CH2:50][OH:51]>>[CH2:50]([O:51][C:14]1[C:19]([C:20]2[NH:21][C:22](=[O:36])[C:23]3[C:24](=[C:26]([CH2:33][CH2:34][CH3:35])[N:27]([CH2:29][CH2:30][O:31][CH3:32])[N:28]=3)[N:25]=2)=[CH:18][C:17]([S:37]([N:40]2[CH2:41][CH2:42][N:43]([CH2:46][CH3:47])[CH2:44][CH2:45]2)(=[O:38])=[O:39])=[CH:16][N:15]=1)[CH:49]([CH3:52])[CH3:48]Participants
4
Conditions
- Temperature
- 120 °C
Procedure
Potassium bis(trimethylsilyl)amide (149.7 mg, 0.75 mmol) was added to a solution of the title compound of example 3 (80 mg, 0.15 mmol) in 2-methyl-n-propanol (5 ml) and the reaction stirred at 120° C. for 18 hours. The cooled mixture was concentrated under reduced pressure and the residue suspended in water (10 ml), and extracted with ethyl acetate (3×10 ml). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel, using an elution gradient of dichloromethane:methanol (100:0 to 95:5) to afford the title compound, 67 mg, as a solid.
Workup
- concentrationThe cooled mixture was concentrated under reduced pressure
- extractionextracted with ethyl acetate (3×10 ml)
- dry with materialThe combined organic extracts were dried (MgSO4)
- customevaporated under reduced pressure
- customThe crude product was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-65eeb03105f041329763f3b947730fec
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07176311B2
Reaction notes
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