Hydrochloric Acid → HCID 10480650, compound

HRID 1391810Notes

Reaction equation

HRID 1391810 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([S:8][C@@H:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[O:30][CH2:31][C:32]([O:34]CC)=[O:33].[OH-].[Na+].Cl>C1COCC1.CO>[CH3:1][C:2]1[CH:7]=[C:6]([S:8][C@@H:9]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)[CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[O:30][CH2:31][C:32]([OH:34])=[O:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58629894HCID 58629894, compound

Product 1

HCID 10480650HCID 10480650, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl {[2-methyl-4-({(1R)-1-[4′-(trifluoromethyl)-4-biphenylyl]pentyl}thio)phenyl]oxy}acetate (10 mg, 0.02 mmol) in THF (1 mL) and MeOH (1 mL) was added aqueous NaOH (2M, 1 mL) and the resulting mixture agitated for 1.5 hours at rt. The mixture was then reduced under vacuum, acidified with aqueous HCl (2M), extracted with DCM (2 mL) and reduced to afford the title compound as colourless oil (9 mg).

Workup

  1. extractionextracted with DCM (2 mL)

Sources & evidence

ORD record
ord-5a0cd5b5f5784a02aeb0f14a9ebc68c3
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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