Sodium hydride → tert-Butyl (3R,6S)-1-(2-methoxyethyl)-2-oxo-6-phenylazepan-3-ylcarbamate

HRID 1768204Notes

Reaction equation

HRID 1768204 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C@H:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][CH2:8][C@H:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][NH:5]1.[CH3:25][O:26][CH2:27][CH2:28]Br>CN(C)C=O>[CH3:25][O:26][CH2:27][CH2:28][N:5]1[CH2:6][C@H:7]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:8][CH2:9][C@@H:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]1=[O:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 23657248tert-butyl (3R,6R)-2-oxo-6-phenylazepan-3-ylcarbamate

Product 1

HCID 86595030tert-Butyl (3R,6S)-1-(2-methoxyethyl)-2-oxo-6-phenylazepan-3-ylcarbamateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 6.2 mg, 0.158 mmol) was added to a solution of tert-butyl (3R,6R)-2-oxo-6-phenylazepan-3-ylcarbamate (40 mg, 0.131 mmol) and 2-bromoethyl methyl ether (0.013 mL, 0.138 mmol) in N,N-dimethylformamide (2 mL) at 0° C. After addition, the mixture was allowed to warm to ambient temperature. After 4 h, the reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was washed with water (3×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (5% ethyl acetate/hexanes→30% ethyl acetate/hexanes) gave the title compound (41 mg). MS 363 (M+1).

Workup

  1. additionAfter addition
  2. customthe reaction was quenched with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water (3×), saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (5% ethyl acetate/hexanes→30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f7adbd55151142bf81cce9763379ddd9
Source dataset
uspto-grants-2007_06
Patent number
US07235545B2

Reaction notes

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