Cesium carbonate → HCID 118199432, compound
Reaction equation
[CH3:1][C:2]1([CH3:33])[O:7][C@H:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:5]([N:17]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])NC(OC(C)(C)C)=O)[CH2:4][O:3]1.C([O-])([O-])=O.[Cs+].[Cs+].BrCC(OC)=O>CC#N>[CH3:1][C:2]1([CH3:33])[O:7][C@H:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH:5]([NH:17][C:26](=[O:27])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:4][O:3]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a suspension of 1,3-ketal-2-hydrazino (8B) (23 mg, 0.05 mmol) and Cs2CO3 (41 mg, 0.13 mmol) in 0.5 mL CH3CN, was added methyl bromoacetate (17 mg, 0.10 mmol) in 0.5 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 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 (90%) (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 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-6529dc9f750b4a4c86ec264ebbe5eb72
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133488B2
Reaction notes
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