Water → HCID 86643142, compound

HRID 1157734Notes

Reaction equation

HRID 1157734 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:34]=[CH:33][C:17]([O:18][C:19]4[CH:20]=[C:21]([C@@:25]5([CH3:32])[O:29][C:28](=[O:30])[NH:27][C:26]5=[O:31])[CH:22]=[CH:23][CH:24]=4)=[C:16]([CH2:35]CC)[CH:15]=3)=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.C([O-])([O-])=[O:39].[Cs+].[Cs+].O>CN(C=O)C>[CH:35]([C:16]1[CH:15]=[C:14]([C:7]2[C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[O:10][C:9](=[O:13])[CH:8]=2)[CH:34]=[CH:33][C:17]=1[O:18][C:19]1[CH:20]=[C:21]([C@@:25]2([CH3:32])[O:29][C:28](=[O:30])[NH:27][C:26]2=[O:31])[CH:22]=[CH:23][CH:24]=1)=[O:39]

Participants

5

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 59396844HCID 59396844, compound

Product 1

HCID 86643142HCID 86643142, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product from step 1 (0.30, 1.0 mmol) and intermediate 13 (0.20, 1.0 mmol) and Cs2CO3 (0.65 g, 2.0 mmol) in DMF (5.0 mL) was stirred at 80° C. for 4 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was washed with water, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to to give the title compound as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a67cc1399cac4217a9ee9c5672dec053
Source dataset
uspto-grants-2010_10
Patent number
US07807692B2

Reaction notes

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