2-Methoxyethanol → HCID 135790112, compound

HRID 1838939Notes

Reaction equation

HRID 1838939 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([O:13][C:14]1[C:19]([C:20]2[NH:21][C:22](=[O:37])[C:23]3[C:24](=[C:26]([CH2:35][CH3:36])[N:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:28]=3)[N:25]=2)=[CH:18][C:17]([S:38]([N:41]2[CH2:46][CH2:45][N:44]([CH2:47][CH3:48])[CH2:43][CH2:42]2)(=[O:40])=[O:39])=[CH:16][N:15]=1)[CH3:12].[CH3:49][O:50]CCO>>[CH2:35]([C:26]1[N:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:28]=[C:23]2[C:22](=[O:37])[NH:21][C:20]([C:19]3[C:14]([O:13][CH2:11][CH2:12][O:50][CH3:49])=[N:15][CH:16]=[C:17]([S:38]([N:41]4[CH2:46][CH2:45][N:44]([CH2:47][CH3:48])[CH2:43][CH2:42]4)(=[O:40])=[O:39])[CH:18]=3)=[N:25][C:24]=12)[CH3:36]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 135469678HCID 135469678, compound

Product 1

HCID 135790112HCID 135790112, compound

Procedure

Potassium bis(trimethylsilyl)amide (294 mg, 1.47 mmol) was added to a solution of the compound from example 66 (200 mg, 0.37 mmol) in 2-methoxyethanol (10 ml), and the reaction heated under reflux for 18 hours. The mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (97:3:0.5) as eluant. The product was recrystallised from dichloromethane:iso-propanol to give the desired compound as a white solid, 82 mg.

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 18 hours
  3. customThe mixture was evaporated under reduced pressure
  4. customthe residue purified by column chromatography on silica gel
  5. customThe product was recrystallised from dichloromethane

Sources & evidence

ORD record
ord-a46371e669b44019ac605c6979755a24
Source dataset
uspto-grants-2004_01
Patent number
US06677335B1

Reaction notes

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