Ethanolamine → tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[(2-hydroxyethyl)amino]methyl}-1,4-oxazepane-4-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2COS(C)(=O)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:29]([CH2:31][NH2:32])[OH:30].[CH2:33](O)C>>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:11][C@H:10]2[CH2:33][NH:32][CH2:31][CH2:29][OH:30])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
4
Conditions
- Temperature
- 80 °C
Procedure
To a solution of tert-butyl (6S,7R)-7-(3,4-dichlorophenyl)-6-{[(methylsulfonyl)oxy]methyl}-1,4-oxazepane-4-carboxylate (1.9 g) in ethanol (41.8 mL) was added ethanolamine (7.57 mL), and the mixture was stirred at 80° C. overnight. The reaction mixture was concentrated under reduced pressure, distilled water was added, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.65 g).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- distillationdistilled water
- additionwas added
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with distilled water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b9adef9a995f4465a7224e412f9c81f1
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722662B2
Reaction notes
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