Potassium Carbonate → HCID 86600805, compound

HRID 33816Notes

Reaction equation

HRID 33816 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][SH:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:19]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][S:41]([CH3:44])(=[O:43])=[O:42])=[CH:36][CH:35]=2)=[CH:27][CH:26]=1)[C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][S:17][CH:19]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][O:33][C:34]3[CH:35]=[CH:36][C:37]([O:40][S:41]([CH3:44])(=[O:42])=[O:43])=[CH:38][CH:39]=3)=[CH:27][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11407297Methyl 2-chloro-3-[4-(2-(4-[(methylsulfonyl)oxy]phenoxy)ethyl)phenyl]propanoateHCID 858420012-[4-(Benzyloxy)phenyl]ethanethiol

Product 1

HCID 86600805HCID 86600805, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[4-(Benzyloxy)phenyl]ethanethiol (334 mg, 1.4 mmol), methyl 2-chloro-3-[4-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)phenyl]propanoate (394 mg, 0.95 mmol) and potassium carbonate (189 mg, 1.4 mmol) were dissolved in 14 ml dry DMF and stirred under nitrogen atmosphere at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was dissolved in toluene. The organic phase was washed (water, brine), dried (MgSO4) and evaporated. Futher purification by preparative HPLC using a gradient of CH3CN/5% CH3CN-waterphase containing 0.1M NH4OAc gave 477 mg of the desired product (yield 75%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in toluene
  3. washThe organic phase was washed (water, brine)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. custompurification by preparative HPLC
  7. additioncontaining 0.1M NH4OAc

Sources & evidence

ORD record
ord-7e798b5632914d01957478e9728e84c8
Source dataset
uspto-grants-2008_09
Patent number
US07429675B2

Reaction notes

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