Hydrochloric Acid → HCID 69114680, compound

HRID 2222930Notes

Reaction equation

HRID 2222930 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH:11]2[C:17]([O:19]CC)=[O:18])=[CH:4][CH:3]=1.[Li+].[OH-].COCCOC.Cl>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH:10]2[CH2:15][CH2:14][CH:13]([CH3:16])[CH2:12][CH:11]2[C:17]([OH:19])=[O:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 80711,2-DimethoxyethaneHCID 86596146HCID 86596146, compound

Product 1

HCID 69114680HCID 69114680, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A solution of (1R/S,3R/S,6R/S)-ethyl 2-{[(4-fluorophenyl)sulfanyl]methyl}-5-methyl-cyclohexanecarboxylate and (1R/S,3S/R,6R/S)-ethyl 2-{[(4-fluorophenyl)sulfanyl]-methyl}-5-methylcyclohexanecarboxylate (1:1 mixture, 54 mg, 0.17 mmol) in a mixture of aqueous LiOH (2 M, 1.7 mL, 3.4 mmol), DME (1 mL) and ethanol (0.3 mL) was heated at 70° C. for 7 h. The solution was cooled to room temperature, acidified with aqueous 2 M HCl (0.5 mL) and extracted with ethyl acetate. The organic extracts were concentrated in vacuo to yield (1R/S,3R/S,6R/S)-2-{[(4-fluorophenyl)sulfanyl]methyl}-5-methylcyclohexanecarboxylic acid and (1R/S,3S/R,6R/S)-2-{[(4-fluorophenyl)sulfanyl]methyl}-5-methylcyclohexanecarboxylic acid as a 1:1 mixture of diastereomers.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-d906e0b5bc46438d9c0f4804168a2877
Source dataset
uspto-grants-2008_05
Patent number
US07371747B2

Reaction notes

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