Water → HCID 21093763, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].C([Li])CCC.[O:22]1[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]1.O>C1COCC1>[Cl:1][C:2]1[C:3]([NH:10][C:11](=[O:16])[C:12]([CH3:13])([CH3:15])[CH3:14])=[C:4]([C:25]2([OH:28])[CH2:26][CH2:27][O:22][CH2:23][CH2:24]2)[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
To a stirred solution of intermediate 12 (1 g, 4.13 mmol) in THF (25 mL) under nitrogen at −20° C. was added dropwise n-butyllithium (2.5M in hexane, 4.13 mL, 10.34 mmol). The reaction mixture was stirred at −10° C. for 4 h and n-butyllithium (2.5M in hexane, 4.13 mL, 10.34 mmol) was added dropwise at −10° C. The mixture was further stirred for 7 h and tetrahydropyran-4-one was added dropwise at 0° C. The mixture was stirred overnight at room temperature, poured into water and extracted with EtOAc. The organic extracts were washed with saturated aqueous NaCl solution, dried over Na2SO4, filtered and concentrated. The crude material was purified by precipitation in EtOAc to afford intermediate 13 as a white powder (0.25 g, 18%).
Workup
- stirringThe mixture was further stirred for 7 h
- stirringThe mixture was stirred overnight at room temperature
- extractionextracted with EtOAc
- washThe organic extracts were washed with saturated aqueous NaCl solution
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by precipitation in EtOAc
Sources & evidence
- ORD record
- ord-d945e50693cd47c3a87a37bf327aa611
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07214676B2
Reaction notes
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