Methyl acetoacetate → tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[4-(methoxycarbonyl)-5-methyl-1H-1,2,3-triazol-1-yl]methyl}-1,4-oxazepane-4-carboxylate

HRID 1022714Notes

Reaction equation

[N:1]([CH2:4][C@H:5]1[C@H:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([Cl:19])[CH:13]=2)[O:10][CH2:9][CH2:8][N:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6]1)=[N+:2]=[N-:3].C(=O)([O-])[O-].[K+].[K+].[C:33]([O:39][CH3:40])(=[O:38])[CH2:34][C:35]([CH3:37])=O>CS(C)=O.C(OCC)(=O)C>[Cl:19][C:14]1[CH:13]=[C:12]([C@@H:11]2[O:10][CH2:9][CH2:8][N:7]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:6][C@H:5]2[CH2:4][N:1]2[C:35]([CH3:37])=[C:34]([C:33]([O:39][CH3:40])=[O:38])[N:3]=[N:2]2)[CH:17]=[CH:16][C:15]=1[Cl:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl (6S,7R)-6-(azidomethyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (200 mg) in DMSO (2 mL) were added potassium carbonate (276 mg) and methyl acetoacetate (0.08 mL) at room temperature, and the mixture was stirred at 80° C. 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 (149 mg).

Workup

washThe diluted solution was washed with distilled water and brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-7d911b32297e4b56b593a80820f0cc77
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722662B2

Reaction notes

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