Sodium periodate → HCID 86619276, compound

HRID 2267617Notes

Reaction equation

HRID 2267617 reaction equation
[CH2:1]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][C@H:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:6]([NH:21][C:22](=[O:37])[C@H:23]([CH3:36])[NH:24][C:25](=[O:35])[CH2:26][C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[C:29]([F:34])[CH:28]=2)[C:5]1=[O:38])[CH:2]=C.I([O-])(=O)(=O)=[O:40].[Na+]>C1COCC1.O.S(=O)(O)[O-].[Na+].O=[Os](=O)(=O)=O>[F:34][C:29]1[CH:28]=[C:27]([CH2:26][C:25]([NH:24][C@H:23]([C:22]([NH:21][C@@H:6]2[C:5](=[O:38])[N:4]([CH2:1][CH:2]=[O:40])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][C@@H:7]2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:37])[CH3:36])=[O:35])[CH:32]=[C:31]([F:33])[CH:30]=1

Participants

7

Reactant 2

HCID 23667635Sodium periodate2×HCID 68605732HCID 68605732, compound

Product 1

HCID 86619276HCID 86619276, compound

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 23665763Sodium BisulfiteSolvent

Procedure

A solution of 63c (582 mg) in THF (10 mL) was treated with a solution sodium periodate (530 mg) in water (10 mL) followed by a 4% solution of OsO4(1 mL). The reaction mixture was stirred for 16 h, diluted with sodium bisulfite solution (20 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were washed with NaCl solution, dried over magnesium sulfate and concentrated under reduced pressure. The product thus obtained was dissolved in THF (50 mL) and treated with a solution sodium periodate (530 mg) in water (50 mL). After stirring for 16 h the reaction mixture was concentrated under reduced pressure and extracted with dichloromethane (2×100 mL). The organic layers were concentrated under reduced pressure and the product was purified by chromatography to obtain the title compound in 1:1 mixture with the (2S,3R) diastereomer (417 mg). 1H NMR (300 MHz, CDCl3) δ 1.05 (m, 3H), 3.47 (two peaks, 2H), 6.74 (m, 2H), 7.25-7.60 (m, 12H).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe organic layers were washed with NaCl solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product thus obtained
  6. stirringAfter stirring for 16 h the reaction mixture
  7. concentrationwas concentrated under reduced pressure
  8. extractionextracted with dichloromethane (2×100 mL)
  9. concentrationThe organic layers were concentrated under reduced pressure
  10. customthe product was purified by chromatography

Sources & evidence

ORD record
ord-2c2cc952f4784caa816a825fc0d048da
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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