Cesium carbonate → HCID 178498214, compound

HRID 2235239Notes

Reaction equation

HRID 2235239 reaction equation
[C:1]([Si:5]([CH3:30])([CH3:29])[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[C:24]([Cl:25])=[CH:23][C:22]([OH:26])=[CH:21][C:20]=3[Cl:27])[C:14]2=[O:28])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[C:31]([O-])([O-])=O.[Cs+].[Cs+].FC[C:39]1[CH:47]=[CH:46][C:42]([C:43]([O-:45])=[O:44])=[CH:41][CH:40]=1>CN(C=O)C.O.CCOC(C)=O>[CH3:31][O:45][C:43](=[O:44])[C:42]1[CH:46]=[CH:47][C:39]([O:26][C:22]2[CH:21]=[C:20]([Cl:27])[C:19]([CH2:18][CH:15]3[CH2:16][CH2:17][N:13]([C@H:10]4[CH2:11][CH2:12][C@@H:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([CH3:30])[CH3:29])[CH2:8][CH2:9]4)[C:14]3=[O:28])=[C:24]([Cl:25])[CH:23]=2)=[CH:40][CH:41]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 17850960p-FluoromethylbenzoateHCID 178455342HCID 178455342, compound

Product 1

HCID 178498214HCID 178498214, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 0.5 g (1 mmol) of 1-[cis-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(2,6-dichloro-4-hydroxy-benzyl)-pyrrolidin-2-one (Preparation 72) 0.7 g (2 mmol) Cs2CO3 and 0.49 g (3 mmol) p-fluoromethylbenzoate in 10 mL dry DMF and heat at 100° C. for 4 hours. Dilute the mixture with 25 mL H2O and 50 mL EtOAc. Separate the layers and extract the aqueous with 50 mL EtOAc. Combine the organic layers, wash with brine, dry over MgSO4 and concentrate under vacuum. Purify via chromatography using 30% EtOAc in hexanes to recover 0.47 g of an oil.

Workup

  1. customSeparate the layers
  2. extractionextract the aqueous with 50 mL EtOAc
  3. washwash with brine
  4. dry with materialdry over MgSO4
  5. concentrationconcentrate under vacuum
  6. customPurify via chromatography
  7. customto recover 0.47 g of an oil

Sources & evidence

ORD record
ord-64eb0807e57c4d5eb17d86359732c21f
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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