Acetyl chloride → tert-butyl (6R,7S)-6-(acetylamino)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022620Notes

Reaction equation

HRID 1022620 reaction equation
[NH2:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[O:7][CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1.C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32]>C1COCC1.C(OCC)(=O)C>[C:31]([NH:1][C@H:2]1[C@H:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=2)[O:7][CH2:6][CH2:5][N:4]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:3]1)(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66975508tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66975754tert-butyl (6R,7S)-6-(acetylamino)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (6R,7S)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (1.3 g) in THF (13 ml) were added triethylamine (0.752 ml) and acetyl chloride (0.385 mL) at 0° C., and the mixture was gradually warmed from 0° C. to room temperature, and stirred overnight. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (0.965 g).

Workup

  1. temperaturethe mixture was gradually warmed from 0° C. to room temperature
  2. washThe diluted solution was washed with distilled water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-8a32c4f09e144d51aa75160da5084277
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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