tert-Butanol → HCID 86630012, compound

HRID 1686062Notes

Reaction equation

HRID 1686062 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:30])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH3:28])=[CH:22][C:21]=1[Cl:29])[CH2:16][CH:17]=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:31]1CCCC1.C(O)(C)(C)C.I([O-])(=O)(=O)=O.[Na+]>[Os](=O)(=O)(=O)=O.O>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:30])[C@H:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH3:28])=[CH:22][C:21]=1[Cl:29])[CH2:16][CH:17]=[O:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8028TetrahydrofuranHCID 23667635Sodium periodateHCID 66671764HCID 66671764, compound

Product 1

HCID 86630012HCID 86630012, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

Treat a mixture of (R)-4-benzyl-3-[(S)-2-(4-methoxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one (6.65 g, 14.87 mmol), tetrahydrofuran (140 mL) and water (45 mL) with 2.5% osmium tetroxide in t-butanol (378 mL, 1.487 mmol). Add sodium periodate (9.55 g, 44.63 mmol) and stir the reaction 4 hr at room temperature. Quench the reaction with water and extract with ethyl acetate. Wash the organic phase with aqueous 1N sodium thiosulfate then brine. Dry the organic layer over magnesium sulfate, filter, and concentrate under vacuum. Purify the crude material by silica gel chromatography using hexanes:ethyl acetate to elute the pure product. Concentrate the fractions containing product under vacuum to afford 3.35 g (49%) of desired product. MS (m/z): 451 (M+).

Workup

  1. additionTreat
  2. customthe reaction 4 hr at room temperature
  3. customQuench
  4. customthe reaction with water
  5. extractionextract with ethyl acetate
  6. washWash the organic phase with aqueous 1N sodium thiosulfate
  7. dry with materialDry the organic layer over magnesium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under vacuum
  10. customPurify the crude material by silica gel chromatography
  11. washethyl acetate to elute the pure product
  12. concentrationConcentrate the fractions
  13. additioncontaining product under vacuum

Sources & evidence

ORD record
ord-0dca0e2a1f1c43da80f15c8c95ed2f3c
Source dataset
uspto-grants-2012_04
Patent number
US08148534B2

Reaction notes

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