Hydrochloric Acid → 3-{4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propenyl]-phenyl}-propionic acid

HRID 2261442Notes

Reaction equation

HRID 2261442 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)=O.[CH3:14][C:15]1([CH3:28])[C@@H:17]2[CH2:18][C:19]3[C:23]([C@H:16]12)=[C:22]([CH3:24])[S:21][C:20]=3[C:25](=[O:27])[CH3:26].[OH-].[K+].Cl>CO.O>[O:27]=[C:25]([C:20]1[S:21][C:22]([CH3:24])=[C:23]2[C:19]=1[CH2:18][C@H:17]1[C:15]([CH3:28])([CH3:14])[C@H:16]12)[CH:26]=[CH:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 198252413-(4-Formylphenyl)propanoic acidHCID 59380608(1aS,5aR)-1-(1,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone

Product 1

HCID 674150403-{4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propenyl]-phenyl}-propionic acidYield 41.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-(4-formyl-phenyl)-propionic acid (142 mg, 0.80 mmol), (1aS,5aR)-1-(1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone (176 mg, 0.80 mmol), KOH (2.8 g, 50 mmol) in methanol (25 mL) is stirred at 70° C. for 1 h. The reaction mixture is diluted with water (400 mL) and acidified by adding 2 N aq. HCl. The mixture is extracted twice with DCM, the organic extracts are combined, dried over Na2SO4 and evaporated. The crude product is purified by prep. HPLC (Waters Xterra MS18 30×75 mm, 10 to 95% acetonitrile in water containing 0.5% formic acid) to give 3-{4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propenyl]-phenyl}-propionic acid (125 mg) as yellow resin; LC-MS: tR=1.07 min, [M+1]+=381.18.

Workup

  1. extractionThe mixture is extracted twice with DCM
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-620cd29050624220ab4a14907844f9ab
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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