2-Methoxyethanol → HCID 135484098, compound

HRID 348408Notes

Reaction equation

HRID 348408 reaction equation
[CH:1]([N:5]1[C:34]([CH2:35][CH3:36])=[C:8]2[N:9]=[C:10]([C:14]3[C:15]([O:31][CH2:32][CH3:33])=[N:16][CH:17]=[C:18]([S:20]([N:23]4[CH2:28][CH2:27][N:26]([CH2:29][CH3:30])[CH2:25][CH2:24]4)(=[O:22])=[O:21])[CH:19]=3)[NH:11][C:12](=[O:13])[C:7]2=[N:6]1)([CH2:3][CH3:4])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:47][O:48]CCO>>[CH:1]([N:5]1[C:34]([CH2:35][CH3:36])=[C:8]2[N:9]=[C:10]([C:14]3[C:15]([O:31][CH2:32][CH2:33][O:48][CH3:47])=[N:16][CH:17]=[C:18]([S:20]([N:23]4[CH2:24][CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH2:28]4)(=[O:21])=[O:22])[CH:19]=3)[NH:11][C:12](=[O:13])[C:7]2=[N:6]1)([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 135462873HCID 135462873, compound

Product 1

HCID 135484098HCID 135484098, compound

Conditions

Temperature
130 °C

Procedure

A solution of the title compound from example 4 (129 mg, 0.25 mmol) in 2-methoxyethanol (10 ml) was heated at 110° C. for 15 minutes, then cooled. Potassium bis(trimethylsilyl)amide (249 mg, 1.50 mmol) was added and the reaction stirred at 130° C. for 22 hours. The cooled mixture was partitioned between ethyl acetate and aqueous sodium bicarbonate solution, and the layers separated. The organic phase was dried (MgSO4) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using dichloromethane:methanol (98:2) as eluant to afford the title compound as a yellow foam, 59 mg.

Workup

  1. temperaturecooled
  2. customThe cooled mixture was partitioned between ethyl acetate and aqueous sodium bicarbonate solution
  3. customthe layers separated
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2fd931a3effc4bce89212dc26a986a7e
Source dataset
uspto-grants-2007_02
Patent number
US07176311B2

Reaction notes

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