Cesium carbonate → HCID 131733499, compound
Reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5](/[CH:6]=[CH:7]/[C@@H:8]2[CH:13]([N:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])NC(OC(C)(C)C)=O)[CH2:12][CH2:11][C:10]([CH3:31])([CH3:30])[O:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(OC)=O>CC#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:6]=[CH:7]/[C@@H:8]2[CH:13]([NH:14][C:23](=[O:24])[O:25][C:26]([CH3:28])([CH3:29])[CH3:27])[CH2:12][CH2:11][C:10]([CH3:31])([CH3:30])[O:9]2)=[CH:32][CH:33]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a suspension of 1,3-ketal-2-hydrazino (8C) (117 mg, 0.24 mmol) and Cs2CO3 (199 mg, 0.61 mmol) in 2.5 mL CH3CN, was added methyl bromoacetate (75 mg, 0.48 mmol) in 1.0 mL CH3CN. The reaction mixture was heated at 50° C. for 3 h. The reaction mixture was then refluxed until the intermediate was consumed as indicated by TLC. The reaction mixture was quenched with saturated NH4Cl (aq.) and extracted with EtOAc. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and the solvent was removed in vacuo. Purification by flash chromatography on silica gel afforded the desired product as a white solid (83%) (Magnus et al., Org. Lett. 2009, 11, 5646).
Workup
- temperatureThe reaction mixture was then refluxed until the intermediate
- customwas consumed
- customThe reaction mixture was quenched with saturated NH4Cl (aq.)
- extractionextracted with EtOAc
- washThe combined organic extracts were washed with brine
- dry with materialdried over anhydrous Na2SO4
- customthe solvent was removed in vacuo
- customPurification by flash chromatography on silica gel
Sources & evidence
- ORD record
- ord-424dbaaaadc2404dba582e6870c59d7f
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133488B2
Reaction notes
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