2-Methoxyethanol → HCID 135816378, compound

HRID 990240Notes

Reaction equation

HRID 990240 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]2[NH:11][C:12](=[O:23])[C:13]3[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=3[N:15]=2)=[CH:8][C:7]([S:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH3:34])[CH2:29][CH2:28]2)(=[O:26])=[O:25])=[CH:6][N:5]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:45][O:46]CCO>>[CH2:33]([N:30]1[CH2:31][CH2:32][N:27]([S:24]([C:7]2[CH:8]=[C:9]([C:10]3[NH:11][C:12](=[O:23])[C:13]4[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][CH2:21][CH3:22])[C:14]=4[N:15]=3)[C:4]([O:3][CH2:1][CH2:2][O:46][CH3:45])=[N:5][CH:6]=2)(=[O:26])=[O:25])[CH2:28][CH2:29]1)[CH3:34]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 3251421Potassium bis(trimethylsilyl)amideHCID 135977905HCID 135977905, compound

Product 1

HCID 135816378HCID 135816378, compoundYield 64%

Procedure

A mixture of the title compound of Example 124 (111 mg, 0.23 mmol) and potassium bis(trimethylsilyl)amide (226 mg, 1.13 mmol) in 2-methoxyethanol (5 ml) was stirred under reflux for 18 hours. The cooled mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel, using dichloromethane: methanol (96:4) as eluant, and triturated with ether to afford the title compound (75 mg, 64%) as a white crystalline solid.

Workup

  1. temperatureunder reflux for 18 hours
  2. customThe cooled mixture was evaporated under reduced pressure
  3. customthe residue purified by column chromatography on silica gel
  4. customtriturated with ether

Sources & evidence

ORD record
ord-483c3bf6410d4161948f8ad75ed237ab
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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