Tetrahydrofuran → HCID 22399013, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:10]([C:12]([O:14]C(OCC)C)=[O:13])[OH:11])=O)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].CS(Cl)(=O)=O.[CH2:43]1[CH2:47][O:46][CH2:45][CH2:44]1>CCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6]1[O:13][C:12](=[O:14])[CH:10]([O:11][CH:45]([O:46][CH2:47][CH3:43])[CH3:44])[C:9]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]=1)([CH3:3])([CH3:2])[CH3:4]Participants
7
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 497 mg (1.16 mmol) of N-tertbutoxycarbonyl-O-(1-ethoxyethyl)-3,3-diphenylisoserine (3) in 20 mL of THF is added 261 mg (2.33 mmol) of solid potassium tert-butoxide and the mixture is stirred at 25° C. for 30 min. A solution of 134 mg (1.16 mmol) of methanesulfonyl chloride in 3.2 mL of THF is added and the mixture is stirred at 25° C. for 1.5 hours. The mixture is diluted with 80 mL of hexane and ethyl acetate, and this solution is extracted with 20 mL of saturated aqueous sodium bicarbonate solution and 10 mL of brine. The organic phase is dried over sodium sulfate and concentrated to give 243 mg (59%) of 2-tertbutoxy-4,4-diphenyl-5-(1-ethoxyethoxy)-4,5-dihydro-1,3-oxazin-6-one as a colorless oil.
Workup
- stirringthe mixture is stirred at 25° C. for 1.5 hours
- extractionthis solution is extracted with 20 mL of saturated aqueous sodium bicarbonate solution and 10 mL of brine
- dry with materialThe organic phase is dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1bf6d056c8f84a45b84d93208643f750
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05384399
Reaction notes
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