Reaction equation
[O:1]=[C:2]1[O:6][CH2:5][C@@H:4]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.CC(C)=[O:20].C([O-])([O-])=O.[Cs+].[Cs+]>O>[OH:20][CH2:5][C@@H:4]([NH:7][C:8]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:17])[CH2:3][C:2]([OH:6])=[O:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In a 500 ml round-bottomed flask phenylmethyl [(3S)-5-oxotetrahydro-3-furanyl]carbamate (4.3 g, 18.28 mmol, available from Sigma-Aldrich # 419249) was dissolved in water (100 ml) and acetone (100 ml) and to this solution Cs2CO3 (10.72 g, 32.9 mmol) was added and the reaction left under stirring at room temperature for 5 hours. The solution was then transferred into a separatory funnel and washed with EtOAc (2×50 ml). The aqueous phase was then acidified to pH=2 by the addition of a 2 M HCl aqueous solution and then extracted with EtOAc (5×100 mls). The organic phase was dried (Na2SO4) and solvent removed under reduced pressure to give the title compound D1 (3.78 g) as a white solid. MS: (ES/+) m/z: 254 (M+1). C12H15NO5 requires 253. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 12.11 (bs, 1 H), 7.41-7.07 (m, 5 H), 5.17-4.92 (m, 2 H), 3.95-3.62 (m, 1 H), 3.42-3.22 (m, 2H), 2.55-2.40 (m, 1 H), 2.34-2.23 (m, 1 H).
Workup
- waitthe reaction left
- customThe solution was then transferred into a separatory funnel
- washwashed with EtOAc (2×50 ml)
- additionThe aqueous phase was then acidified to pH=2 by the addition of a 2 M HCl aqueous solution
- extractionextracted with EtOAc (5×100 mls)
- dry with materialThe organic phase was dried (Na2SO4) and solvent
- customremoved under reduced pressure
Sources & evidence
- ORD record
- ord-e541810d00e048ceb3fa3ad3bc41bdc7
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08133908B2
Linked notes
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