Pyridine, hydrofluoride (1:1) → HCID 11656125, compound

HRID 1375697Notes

Reaction equation

HRID 1375697 reaction equation
[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[CH:17]([O:30][Si](C(C)(C)C)(C)C)[CH2:18][CH2:19][C:20]2[S:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[C:21]=2[Cl:29])[CH2:13][CH:12]([OH:38])[C:11]1=[O:39].C1C=CN=CC=1.F.C([O-])(O)=O.[Na+]>C(#N)C>[CH3:1][O:2][C:3](=[O:40])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14](/[CH:15]=[CH:16]/[CH:17]([OH:30])[CH2:18][CH2:19][C:20]2[S:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[C:21]=2[Cl:29])[CH2:13][CH:12]([OH:38])[C:11]1=[O:39]

Participants

5

Reactant 3

HCID 64774Pyridine, hydrofluoride (1:1)HCID 516892Sodium BicarbonateHCID 68677414HCID 68677414, compound

Product 1

HCID 11656125HCID 11656125, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An acetonitrile (0.35 mL) solution of 7 (9 mg, 0.015 mmol) was treated with HF-pyridine (0.07 mL). The solution was allowed to stir for 2 h and then 20 mL of saturated NaHCO3 solution was added. The mixture was extracted with dichloromethane (3×15 mL) and the combined dichloromethane solution dried (Na2SO4), filtered and evaporated. Purification by preparative thin layer chromatography (50% ethyl acetate/hexanes) gave two diastereomers of diol 8 (2 mg each, 0.004 mmol each, 27% for each).

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×15 mL)
  2. dry with materialthe combined dichloromethane solution dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by preparative thin layer chromatography (50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bbdf21a0e18042c09d300496aca21fab
Source dataset
uspto-grants-2007_01
Patent number
US07169807B2

Reaction notes

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