Hydrochloric Acid → HCID 10481273, compound

HRID 1391812Notes

Reaction equation

HRID 1391812 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([S:8]([CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[N:16]=2)[CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])[CH:5]=[CH:4][C:3]=1[O:31][CH2:32][C:33]([O:35]CC)=[O:34].[OH-].[Na+].Cl>C1COCC1.CO.O>[CH3:1][C:2]1[CH:7]=[C:6]([S:8]([CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)[N:16]=2)[CH2:11][CH2:12][CH2:13][CH3:14])=[O:9])[CH:5]=[CH:4][C:3]=1[O:31][CH2:32][C:33]([OH:35])=[O:34]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58629870HCID 58629870, compound

Product 1

HCID 10481273HCID 10481273, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of ethyl ({2-methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}pentyl)sulfinyl]phenyl}oxy)acetate (27 mg, 0.05 mmol) in THF (1 mL) and methanol (1 mL) was added, drop-wise, aqueous NaOH (2M, 1 mL). After 2 hours 50 minutes the mixture was concentrated producing a ‘chalk-white’ solid which was diluted with water (2 mL) and acidified with aqueous HCl (2M, 2 mL). The aqueous layer was extracted with DCM (2×2 mL then 1 mL) using a hydrophobic frit and the combined organic layer concentrated under vacuum yielding the title compound as a mixture of two diastereoisomers (24 mg).

Workup

  1. concentrationAfter 2 hours 50 minutes the mixture was concentrated
  2. customproducing a ‘chalk-white’ solid which
  3. extractionThe aqueous layer was extracted with DCM (2×2 mL
  4. concentrationthe combined organic layer concentrated under vacuum

Sources & evidence

ORD record
ord-812ed020aa074010b82f8fadd20d1a3d
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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