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

HRID 2261443Notes

Reaction equation

HRID 2261443 reaction equation
[O:1]=[C:2]([C:16]1[S:23][C:22]([CH3:24])=[C:21]2[C:17]=1[CH2:18][C@H:19]1[C:25]([CH3:27])([CH3:26])[C@H:20]12)[CH:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1>C(O)C.[Pd]>[O:1]=[C:2]([C:16]1[S:23][C:22]([CH3:24])=[C:21]2[C:17]=1[CH2:18][C@H:19]1[C:25]([CH3:27])([CH3:26])[C@H:20]12)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1

Participants

4

Reactant 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 acid

Product 1

HCID 674157373-{4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenyl}-propionic acidYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 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 (121 mg, 0.32 mmol), Pd/C (40 mg, 10% Pd) in ethanol (8 mL) is stirred at rt under 1 bar H2. The reaction mixture is filtered, the filtrate is evaporated 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)-propyl]-phenyl}-propionic acid (120 mg) as a pale yellow oil; LC-MS: tR=1.07 min, [M+1]+=383.17.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-077cb4a7a5254c1c843e499d58aa54a8
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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