Sodium Hydroxide → 3-((3-(2-Acetylphenyl)-1-(3-((2-tetrahydropyranyloxy)methyl)phenyl)propyl)thio)-2-methylpropanoic acid

HRID 341990Notes

Reaction equation

HRID 341990 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH:12]([S:27][CH2:28][CH:29]([CH3:35])[C:30]([O:32]CC)=[O:31])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:14]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][CH:12]([S:27][CH2:28][CH:29]([CH3:35])[C:30]([OH:32])=[O:31])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:14]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54537147HCID 54537147, compound

Product 1

HCID 538849643-((3-(2-Acetylphenyl)-1-(3-((2-tetrahydropyranyloxy)methyl)phenyl)propyl)thio)-2-methylpropanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of the ester of Step 7 (6.67 mmol) and 1.0N NaOH (13 mL) in 55 mL of MeOH:THF 3:2 was stirred at r.t. for 24 hours. 25% Aq NH4OAc was then added and the mixture was acidified with HOAC. The title acid was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with acetone:toluene:HOAc.

Workup

  1. extractionThe title acid was extracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. custompurified by flash chromatography on silica with acetone

Sources & evidence

ORD record
ord-a33b053c8a2b48f0add51d281ca69c20
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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