5-{3-[(1s,5s)-5-(3-Chloro-5-hydroxymethyl-phenoxymethyl)-4-oxo-cyclopent-2-enyl]-propyl}-thiophene-2-carboxylic acid → HCID 23658434, compound

HRID 33768Notes

Reaction equation

HRID 33768 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([CH2:27][OH:28])[CH:26]=1)[O:5][CH2:6][C@@H:7]1[C@@H:11]([CH2:12][CH2:13][CH2:14][C:15]2[S:19][C:18]([C:20]([OH:22])=[O:21])=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:8]1=[O:23].[H][H]>[Pd].CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[C:25]([CH2:27][OH:28])[CH:26]=1)[O:5][CH2:6][C@H:7]1[C:8](=[O:23])[CH2:9][CH2:10][C@@H:11]1[CH2:12][CH2:13][CH2:14][C:15]1[S:19][C:18]([C:20]([OH:22])=[O:21])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 236343805-{3-[(1s,5s)-5-(3-Chloro-5-hydroxymethyl-phenoxymethyl)-4-oxo-cyclopent-2-enyl]-propyl}-thiophene-2-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 23658434HCID 23658434, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon (10 wt. %, 1 mg) was added to a mixture of 12 and 13 (10 mg, ˜0.022 mmol) in EtOAc (0.42 mL). A hydrogen atmosphere was established by evacuating and refilling with hydrogen (10×) and the reaction mixture was stirred under a balloon of hydrogen for 6 h. The reaction mixture was filtered through celite, washing with EtOAc, and the filtrate was concentrated in vacuo. Purification of the resulting crude residue by flash column chromatography on silica gel (10% MeOH/CH2Cl2) afforded 7 mg (˜68%) of ester 14 and 2.7 mg (30%) of title compound 15.

Workup

  1. customby evacuating
  2. filtrationThe reaction mixture was filtered through celite
  3. washwashing with EtOAc
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification of the resulting crude residue by flash column chromatography on silica gel (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-34e9558429f245c899a6b2d53d2ae725
Source dataset
uspto-grants-2008_09
Patent number
US07429669B2

Reaction notes

Loading…