Ethyl Acetate → t-Butyl alpha-[3(S*)-azido-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetate

HRID 569755Notes

Reaction equation

HRID 569755 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H-].[Na+].[N:12]([C@@H:15]1[CH2:21][CH2:20][C@@H:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][NH:17][C:16]1=[O:28])=[N+:13]=[N-:14].C(OCC)(=O)C>CN(C)C=O.O>[N:12]([C@@H:15]1[CH2:21][CH2:20][C@@H:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:18][N:17]([CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:16]1=[O:28])=[N+:13]=[N-:14]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 140034353(S*)-Azido-6(R*)-phenylperhydroazepin-2-one

Product 1

HCID 14003443t-Butyl alpha-[3(S*)-azido-2-oxo-6(R*)-phenylperhydroazepin-1-yl]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.9 ml of t-butyl bromoacetate followed by 219 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added, under a stream of nitrogen, to a solution of 1.05 g of 3(S*)-azido-6(R*)-phenylperhydroazepin-2-one (Isomer A) [prepared as described in Example 1(f)] in 10 ml of dimethylformamide, whilst ice-cooling. The mixture was stirred for 1.5 hours, and then ethyl acetate and water were added. The ethyl acetate layer was separated, washed with water, and dried over anhydrous magnesium sulfate. The solvent was then distilled off. The residue was purified by silica gel column chromatography using a 1:4 by volume mixture of ethyl acetate and cyclohexane as eluent, to give 1.54 g of the title compound as crystals, melting at 119°-121° C.

Workup

  1. temperaturewhilst ice-cooling
  2. customThe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off
  6. customThe residue was purified by silica gel column chromatography
  7. additionby volume mixture of ethyl acetate and cyclohexane as eluent

Sources & evidence

ORD record
ord-fea1c6b223c245bfa5827ddd55dd5a4a
Source dataset
uspto-grants-1988_03
Patent number
US04734410

Reaction notes

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