{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acid → {3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl-sulfanyl]propylsulfanyl}acetic Acid Isopropyl Ester

HRID 2187970Notes

Reaction equation

HRID 2187970 reaction equation
[CH:1](NN=NC1C=CC(C)=CC=1)([CH3:3])[CH3:2].[OH:14][C@@H:15]1[CH2:19][C:18](=[O:20])[C@H:17]([S:21][CH2:22][CH2:23][CH2:24][S:25][CH2:26][C:27]([OH:29])=[O:28])[C@H:16]1/[CH:30]=[CH:31]/[C@@H:32]([OH:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CC(C)=O>[CH:1]([O:28][C:27](=[O:29])[CH2:26][S:25][CH2:24][CH2:23][CH2:22][S:21][C@H:17]1[C:18](=[O:20])[CH2:19][C@@H:15]([OH:14])[C@@H:16]1/[CH:30]=[CH:31]/[C@@H:32]([OH:38])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9886718{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-5-oxocyclopentylsulfanyl]propylsulfanyl}acetic acidHCID 178426646HCID 178426646, compound

Product 1

HCID 9802877{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl-sulfanyl]propylsulfanyl}acetic Acid Isopropyl EsterYield 38%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Isopropyl-p-tolyltriazene (200 μL) was added dropwise to a solution of carboxylic acid 9 (10.5 mg, 0.026 mmol) in acetone (5.0 mL) at 23° C. After stirring for 1 h the reaction was quenched with 1N HCl and the solvent was removed in vacuo. The residue was extracted with CH2Cl2 (2×). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 4:1 hex/EtOAc) gave 4.3 mg (38%) of the above titled compound.

Workup

  1. customwas quenched with 1N HCl
  2. customthe solvent was removed in vacuo
  3. extractionThe residue was extracted with CH2Cl2 (2×)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash column chromatography (silica gel, 4:1 hex/EtOAc)

Sources & evidence

ORD record
ord-c7d6a72a9949499fbe3d45b13de6c368
Source dataset
uspto-grants-2002_06
Patent number
US06410591B1

Reaction notes

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