Hydrochloric Acid → HCID 10254973, compound

HRID 1391811Notes

Reaction equation

HRID 1391811 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([S:8][C@H:9]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[N: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:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[N:15]=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 58629930HCID 58629930, compound

Product 1

HCID 10254973HCID 10254973, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl ({2-methyl-4-[((1S)-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)thio]phenyl}oxy)acetate (34 mg, 0.07 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) and extracted with DCM (2 mL) and reduced to afford the title compound as a colourless oil (31 mg).

Workup

  1. extractionextracted with DCM (2 mL)

Sources & evidence

ORD record
ord-0b88fab500e34330a101a6c1e6754b4c
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

Loading…