Hydrochloric Acid → (1R,2R)-2-(4-Chloro-phenoxymethyl)-4-(2-chloro-phenylsulfanyl)-cyclopentanecarboxylic acid ethyl ester

HRID 1367490Notes

Reaction equation

HRID 1367490 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[H-].[Na+].[CH2:11]([O:13][C:14]([C@@H:16]1[CH2:20][CH:19](OS(C)(=O)=O)[CH2:18][C@H:17]1[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=[O:15])[CH3:12].Cl>O1CCCC1>[CH2:11]([O:13][C:14]([C@@H:16]1[CH2:20][CH:19]([S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:18][C@H:17]1[CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)=[O:15])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 80599o-ChlorothiophenolHCID 86649021(1R,2R)-2-(4-Chloro-phenoxymethyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 66918839(1R,2R)-2-(4-Chloro-phenoxymethyl)-4-(2-chloro-phenylsulfanyl)-cyclopentanecarboxylic acid ethyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-chlorobenzenthiol (306 mg) in tetrahydrofuran (4 mL) was added a suspension of sodium hydride in oil (55% w/w, 107 mg). The white suspension was cooled down to 0° C. then a solution of (1R,2R)-2-(4-Chloro-phenoxymethyl)-4-methanesulfonyloxy-cyclopentanecarboxylic acid ethyl ester (epimeric mixture, 343 mg) in tetrahydrofuran (5 mL) was slowly added. The reaction mixture was stirred at room temperature for 4 days. Hydrochloric acid (1N) was added and the mixture was extracted with ethyl acetate. The combined organic layers were washed with an aqueous saturated solution of sodiumcarbonate and brine then dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethylacetate (19:1 to 3:1 v/v) as eluant to afford the title compound (0.205 g, 53%) as light yellow oil. MS (EI): 424.0 (M+H)+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layers were washed with an aqueous saturated solution of sodiumcarbonate and brine
  3. dry with materialthen dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/ethylacetate (19:1 to 3:1 v/v) as eluant

Sources & evidence

ORD record
ord-69a3536bcfb6409a9abdad0273579b97
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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