Sodium hydride → HCID 86611789, compound
Reaction equation
[C:1]([NH:8][OH:9])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH2:12]([O:14][C:15](=[O:30])[CH:16](OS(C)(=O)=O)[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:13]>CN(C=O)C>[CH2:12]([O:14][C:15](=[O:30])[CH:16]([O:9][NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of BocNHOH (958 mg, 7.2 mmol) in DMF (15 mL) was added NaH (60% in mineral oil, 320 mg, 8 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 15 min. The compound from Step 9a (1.81 g, 6 mmol) was added to the mixture at 0° C. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated NH4Cl and extracted with EtOAc (3×15 mL), dried (Na2SO4) and filtered. The organic solvent was removed under reduced pressure and residue was purified by flash chromatography (Hexanes/EtOAc=3/1), giving 1 g (50%) of the title compound. 13C NMR (CDCl3): δ17172.0, 156.6, 141.3, 128.8, 128.7, 126.3, 83.3, 82.2, 61.5, 33.0, 31.7, 28.5, 14.5.
Workup
- stirringThe resulting mixture was stirred at room temperature for 2 hours
- customThe reaction mixture was quenched with saturated NH4Cl
- extractionextracted with EtOAc (3×15 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customThe organic solvent was removed under reduced pressure and residue
- customwas purified by flash chromatography (Hexanes/EtOAc=3/1)
Sources & evidence
- ORD record
- ord-cee19ef11b5446b39f25c13ff7565638
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589067B2
Reaction notes
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