Hydrofluoric Acid → HCID 57206089, compound

HRID 487826Notes

Reaction equation

HRID 487826 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]([CH3:53])=[CH:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH:47]([O:51][CH3:52])[CH2:46]2)[CH:8]([CH3:54])[CH:7]([O:55][Si](C(C)(C)C)(C)C)[CH2:6][C:5]1=[O:63])[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]([CH3:53])=[CH:44][CH:45]2[CH2:50][CH2:49][CH2:48][CH:47]([O:51][CH3:52])[CH2:46]2)[CH:8]([CH3:54])[CH:7]([OH:55])[CH2:6][C:5]1=[O:63])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 57226268HCID 57226268, compound

Product 1

HCID 57206089HCID 57206089, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product of step (c) (40 mg) in acetonitrile (8 ml) was added 40% aqueous hydrofluoric acid (1 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 ether extracts were then dried (MgSO4), filtered and concentrated to an oil in vacuo. Chromatography on silica eluting with hexane in an increasing acetone gradient then gave the title compound as a foam (20 mg).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. dry with materialThe ether extracts were then dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to an oil in vacuo

Sources & evidence

ORD record
ord-9603f75f76964fa197e17b984512f14f
Source dataset
uspto-grants-1994_03
Patent number
US05296489

Reaction notes

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