Isobutanol → HCID 135790110, compound

HRID 348407Notes

Reaction equation

HRID 348407 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:35])[C:23]3[C:24](=[C:26]([CH2:33][CH3:34])[N:27]([CH2:29][CH2:30][O:31][CH3:32])[N:28]=3)[N:25]=2)=[CH:18][C:17]([S:36]([N:39]2[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]2)(=[O:38])=[O:37])=[CH:16][N:15]=1)C.[CH3:46][CH:47]([CH3:50])[CH2:48][OH:49]>>[CH2:48]([O:49][C:14]1[C:19]([C:20]2[NH:21][C:22](=[O:35])[C:23]3[C:24](=[C:26]([CH2:33][CH3:34])[N:27]([CH2:29][CH2:30][O:31][CH3:32])[N:28]=3)[N:25]=2)=[CH:18][C:17]([S:36]([N:39]2[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]2)(=[O:37])=[O:38])=[CH:16][N:15]=1)[CH:47]([CH3:50])[CH3:46]

Participants

4

Reactant 3

HCID 6560IsobutanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 135484059HCID 135484059, compound

Product 1

HCID 135790110HCID 135790110, compound

Procedure

Potassium bis(trimethylsilyl)amide (306 mg, 1.54 mmol) was added to a solution of the title compound of example 2 (155 mg, 0.31 mmol) in 2-methyl-n-propanol (10 ml) and the reaction stirred under reflux for 24 hours. The cooled mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel, using an elution gradient of dichloromethane:methanol (100:0 to 95:5) to afford the title compound, 88 mg, as a solid.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe cooled mixture was evaporated under reduced pressure
  3. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-49ef2b9ab2904d7faf86e0aa9777f8b6
Source dataset
uspto-grants-2007_02
Patent number
US07176311B2

Reaction notes

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