Triphenylphosphine → (+)-Ethyl 2-ethoxy-3-[4-[2-[4-oxo-3,4-dihydro-1,3-benzoxazin-3-yl]ethoxy]phenyl]propanoate
Reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[O:6][CH2:5]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:34]([O:36][CH:37]([CH2:43][C:44]1[CH:49]=[CH:48][C:47](O)=[CH:46][CH:45]=1)[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH3:35].C(OC([N+](C(OC(C)C)=O)=[N-])=O)(C)C>C1(C)C=CC=CC=1.O>[CH2:34]([O:36][CH:37]([CH2:43][C:44]1[CH:45]=[CH:46][C:47]([O:1][CH2:2][CH2:3][N:4]2[C:9](=[O:10])[C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[O:6][CH2:5]2)=[CH:48][CH:49]=1)[C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH3:35]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred mixture of 3-(2-hydroxyethyl)-4-oxo-3,4-dihydro-1,3-benzoxazine (325 mg, 1.68 mmol) and triphenylphosphine (660 mg, 2.52 mmol) in toluene (10 mL) was added a solution of (+)-ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate (400 mg, 1.68 mmol) at 25° C. and stirred for 10 min. To the reaction mixture was added diisopropyldiazodicarboxylate (0.5 mL, 2.52 mmol) at 25-30° C. and stirred for further 40 h. Water was added to the reaction mixture and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was chromatographed on silica gel using a gradient of 5-15% ethyl acetate in pet ether as eluent to afford the title compound (527 mg, 76%): mp 76-78° C.
Workup
- stirringstirred for further 40 h
- extractionextracted with ethyl acetate (3×10 mL)
- washThe combined organic extracts were washed with brine
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated
- customThe residue was chromatographed on silica gel using a gradient of 5-15% ethyl acetate in pet ether as eluent
Sources & evidence
- ORD record
- ord-4646b01659524c8590fa560b9eb12837
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06130214
Reaction notes
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