Tetrahydrofuran → HCID 131715184, compound

HRID 652752Notes

Reaction equation

HRID 652752 reaction equation
[CH2:1]([S:7][CH2:8][CH:9]1[CH:14]2[O:15][CH:11]([CH2:12][CH2:13]2)[CH:10]1[CH2:16][CH:17]=[CH:18][CH2:19][CH2:20][C:21]([CH3:34])([CH3:33])[C:22](=[N:31]O)[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].I([O-])(=O)(=O)=[O:36].[Na+].O1CCCC1>CO>[CH2:1]([S:7]([CH2:8][CH:9]1[CH:14]2[O:15][CH:11]([CH2:12][CH2:13]2)[CH:10]1[CH2:16][CH:17]=[CH:18][CH2:19][CH2:20][C:21]([CH3:34])([CH3:33])[C:22](=[NH:31])[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 131715185HCID 131715185, compound

Product 1

HCID 131715184HCID 131715184, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 634 mg (1.72 mmol) of [1α,2β(5Z),3β,4α]-7-[3-([hexylthio)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-2,2-dimethyl-5-heptenimidic acid, phenylmethyl ester (prepared as described in Example 17) in 6.78 ml of methanol at 0° C. is added dropwise over 4 minutes 4.8 ml of 0.5M aqueous sodium periodate solution. Tetrahydrofuran (2 ml) is then added and the resulting reaction mixture is stirred at room temperature for 15 hours. A precipitate is removed by filtration and washed with ether (3×50 ml). The filtrate is washed with 60 ml of saturated aqueous NaHCO3 solution and dried over anhydrous magnesium sulfate. Concentration in vacuo affords an oily crude product. This is chromatographed on silica gel 60 using 0.5-1.0% CH3OH in CH2Cl2 as eluant. This gives [1α,2β(5Z),3β,4α]- 7-[3-[(hexylsulfinyl)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-2,2-dimethyl-5-heptenimidic acid, phenylmethyl ester and [1α,2β(5Z),3β,4α]-7-[3-[(hexylsulfonyl)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-2,2-dimethyl-5-heptenimidic acid, phenylmethyl ester.

Workup

  1. customthe resulting reaction mixture
  2. customA precipitate is removed by filtration
  3. washwashed with ether (3×50 ml)
  4. washThe filtrate is washed with 60 ml of saturated aqueous NaHCO3 solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationConcentration in vacuo
  7. customaffords an oily crude product
  8. customThis is chromatographed on silica gel 60 using 0.5-1.0% CH3OH in CH2Cl2 as eluant

Sources & evidence

ORD record
ord-07a6703542144364aa9b482d66de75d1
Source dataset
uspto-grants-1987_06
Patent number
US04673685

Reaction notes

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