Potassium bis(trimethylsilyl)amide → HCID 135816395, compound

HRID 990231Notes

Reaction equation

HRID 990231 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:39])[C:23]3[C:24](=[C:26]([CH2:36][CH2:37][CH3:38])[N:27]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)[N:28]=3)[N:25]=2)=[CH:18][C:17]([S:40]([N:43]2[CH2:48][CH2:47][N:46]([CH2:49][CH3:50])[CH2:45][CH2:44]2)(=[O:42])=[O:41])=[CH:16][N:15]=1)[CH3:12]>OCC1C=COC=1>[CH2:49]([N:46]1[CH2:47][CH2:48][N:43]([S:40]([C:17]2[CH:18]=[C:19]([C:20]3[NH:21][C:22](=[O:39])[C:23]4[C:24](=[C:26]([CH2:36][CH2:37][CH3:38])[N:27]([CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=5)[N:28]=4)[N:25]=3)[C:14]([O:13][CH2:11][C:12]3[CH:12]=[CH:11][O:13][CH:14]=3)=[N:15][CH:16]=2)(=[O:41])=[O:42])[CH2:44][CH2:45]1)[CH3:50]

Participants

4

Reactant 2

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 135485687HCID 135485687, compound

Product 1

HCID 135816395HCID 135816395, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 204493-FuranmethanolSolvent

Procedure

Potassium bis(trimethylsilyl)amide (176 mg, 0.88 mmol) was added to a stirred suspension of the title compound of Example 26 (100 mg, 0.17 mmol) in 3-hydroxymethylfuran (4 ml) and the reaction mixture heated under reflux for 24 hours then allowed to cool. The resulting mixture was evaporated under reduced pressure and the residue purified by column chromatography on silica gel, using dichloromethane:methanol (95:5) as eluant, to furnish the title compound (33 mg, 31%) as a pale yellow foam. δ (CDCl3) 0.93 (3H, t), 1.04 (3H, t), 1.72 (2H, m), 2.41 (2H, q), 2.55 (4H, m), 2.99 (2H, t), 3.14 (4H, m), 5.63 (2H, s), 5.68 (2H, s), 6.60 (1H, s), 7.09 (1H, d), 7.22 (1H, m), 7.44 (1H, s), 7.64 (2H, m), 8.57 (1H, d), 8.68 (1H, s), 9.02 (1H, s), 10.53 (1H, s). LRMS: m/z 619 (M+1)+.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 24 hours
  3. temperatureto cool
  4. customThe resulting mixture was evaporated under reduced pressure
  5. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cc30fd7d4dc84e23a6d1460d0b7a15fe
Source dataset
uspto-grants-2002_10
Patent number
US06458951B2

Reaction notes

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