Pyridine, hydrofluoride (1:1) → {3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl-sulfanyl]propylsulfanyl}acetic Acid Methyl Ester

HRID 1862489Notes

Reaction equation

HRID 1862489 reaction equation
N1C=CC=CC=1.F.[CH3:8][O:9][C:10](=[O:47])[CH2:11][S:12][CH2:13][CH2:14][CH2:15][S:16][C@H:17]1[C:21](=[O:22])[CH2:20][C@@H:19]([O:23][Si](C(C)(C)C)(C)C)[C@@H:18]1/[CH:31]=[CH:32]/[C@@H:33]([O:39][Si](C(C)(C)C)(C)C)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]>CC#N>[CH3:8][O:9][C:10](=[O:47])[CH2:11][S:12][CH2:13][CH2:14][CH2:15][S:16][C@H:17]1[C:21](=[O:22])[CH2:20][C@@H:19]([OH:23])[C@@H:18]1/[CH:31]=[CH:32]/[C@@H:33]([OH:39])[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 12990739(3-{(1R,2S,3R)-3-(tert-Butyldimethylsilanyloxy)-2-[(S)-(E)-3-(tert-butyldimethylsilanoxy)oct-1-enyl]-5-oxocyclopentylsulfanyl} propylsulfanyl)acetic acid methyl ester

Product 1

HCID 10111873{3-[(1R,2S,3R)-3-Hydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl-sulfanyl]propylsulfanyl}acetic Acid Methyl EsterYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Hydrogen fluoride-pyridine (220 μL) was added to a solution of bis-TBDMS ether 7 (70 mg, 0.11 mmol) in CH3CN (2.0 mL) at 0° C. The reaction was warmed to room temperature, stirred 1 h, and recooled to 0° C. The reaction was quenched with saturated aqueous NaHCO3 until gas evolution ceased. The mixture was extracted with CH2Cl2 (4×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 100% CH2Cl2 followed by 30:1 CH2Cl2:MeOH) provided 40 mg (90%) of the above titled compound.

Workup

  1. customrecooled to 0° C
  2. customThe reaction was quenched with saturated aqueous NaHCO3 until gas evolution
  3. extractionThe mixture was extracted with CH2Cl2 (4×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography (silica gel, 100% CH2Cl2 followed by 30:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-ab1f099447b9408dbf398d1842c0674c
Source dataset
uspto-grants-2003_03
Patent number
US06538018B1

Reaction notes

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