Water → HCID 67182870, compound

HRID 84029Notes

Reaction equation

HRID 84029 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].CS(O[CH2:18][CH2:19][C@H:20]1[C@@H:27]2[C@@H:23]([O:24][C:25]([CH3:29])([CH3:28])[O:26]2)[O:22][C@@H:21]1[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1)(=O)=O.C(OCC)(=O)C.O>CN(C)C=O>[Cl:44][C:41]1[CH:42]=[CH:43][C:38]([C:35]2[CH:34]=[CH:33][C:32]([CH2:31][CH2:30][C@H:21]3[O:22][C@@H:23]4[O:24][C:25]([CH3:28])([CH3:29])[O:26][C@@H:27]4[C@@H:20]3[CH2:19][CH2:18][N:5]3[C:1](=[O:11])[C:2]4[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:4]3=[O:6])=[CH:37][CH:36]=2)=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24194345Phthalimide potassium saltHCID 867009772-{(3aR,5R,6R,6aR)-5-[2-(4'-chlorobiphenyl-4-yl)ethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}ethyl methanesulfonate

Product 1

HCID 67182870HCID 67182870, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Potassium phthalimide (0.051 g) was added in one portion to a stirred solution of the compound obtained from step j above (0.12 g) in dimethylformamide (5 mL) at room temperature under a nitrogen atmosphere. The resulting solution was heated at 50° C. for about 14 hours and then cooled to room temperature. Ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous sodium sulphate. The organic phase was evaporated to dryness under reduced pressure. The residue thus obtained was purified by column chromatography using 30% ethyl acetate in hexane as eluant to furnish the title compound (0.1 g).

Workup

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. customThe organic phase was evaporated to dryness under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-477abb63f8c64523a768253485779b73
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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