Hydrofluoric Acid → HCID 57206900, compound

HRID 487824Notes

Reaction equation

HRID 487824 reaction equation
[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][C@H:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:8]([CH3:55])[CH:7]([O:56][Si](C(C)(C)C)(C)C)[CH2:6][C:5]1=[O:64])[CH:2]=[CH2:3].F.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][C@H:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:8]([CH3:55])[CH:7]([OH:56])[CH2:6][C:5]1=[O:64])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 131718365HCID 131718365, compound

Product 1

HCID 57206900HCID 57206900, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product of step (d) (0.28 g) in acetonitrile (10 ml) was added 40% aqueous hydrofluoric acid (2 ml). After stirring for 1 hour at room temperature the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and the mixture was extracted with diethyl ether. The organic extract was then dried (MgSO4), filtered and evaporated to an oil in vacuo. Chromatography on silica eluting with acetone/hexane [1:2] then gave the title compound (0.22 g) as a foam.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. extractionThe organic extract
  3. dry with materialwas then dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to an oil in vacuo

Sources & evidence

ORD record
ord-69736cbad9ea4efcba36633e74b09281
Source dataset
uspto-grants-1994_03
Patent number
US05296489

Reaction notes

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