Sodium hydride → HCID 15908912, compound

HRID 429722Notes

Reaction equation

HRID 429722 reaction equation
[H-].[Na+].[Br:3][CH:4]1[CH2:10][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH2:8][CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:6][C:5]1=[O:24].C([CH:29](I)[C:30]([NH2:32])=[O:31])(C)(C)C>>[C:9]([NH:32][C:30](=[O:31])[CH2:29][N:6]1[CH:7]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH2:10][CH:4]([Br:3])[C:5]1=[O:24])([CH3:11])([CH3:10])[CH3:8]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 18352660HCID 18352660, compoundHCID 18352670HCID 18352670, compound

Product 1

HCID 15908912HCID 15908912, compoundYield 184.9%

Procedure

To a 1000 mL 3-necked round-bottomed flank equipped with addition funnel and nitrogen inlet was added 3.9 grams (97.6 mmol) sodium hydride, which was then washed with hexane, and 400 mL dry tetrahydrofuran. To the stirring suspension was added a solution of 31.8 grams (88.8 mmol) 3-Bromo-5-(2-methylphenyl)-7-phenyl-2,3,4,5,6,7-hexahydroazepin-2-one and 23.5 grams (97.6 mmol) t-butyl iodoacetamide. The reaction was stirred at room temperature for 60 hours, quenched with ammonium chloride solution, then poured into water, extracted twice into ethyl acetate, washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using 2/1-hexane/ethyl acetate an eluent to afford 38.7 grams (92%) of a foam, a mixture of diastereomers.

Workup

  1. customTo a 1000 mL 3-necked round-bottomed flank equipped with addition funnel and nitrogen inlet
  2. washwas then washed with hexane, and 400 mL dry tetrahydrofuran
  3. customquenched with ammonium chloride solution
  4. additionpoured into water
  5. extractionextracted twice into ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel using 2/1-hexane/ethyl acetate an eluent

Sources & evidence

ORD record
ord-ffda83f525a74c99b88ba20fbc87f5c8
Source dataset
uspto-grants-2001_11
Patent number
US06319915B1

Reaction notes

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