Hydrofluoric Acid → Methyl (3R,6E)-7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3-hydroxy-5-oxo-6-heptenoate

HRID 649710Notes

Reaction equation

HRID 649710 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16](=[O:32])[CH2:17][C@@H:18]([O:24][Si](C(C)(C)C)(C)C)[CH2:19][C:20]([O:22][CH3:23])=[O:21])=[C:12]([CH:33]([CH3:35])[CH3:34])[N:11]=[C:10]([N:36]([CH3:41])[S:37]([CH3:40])(=[O:39])=[O:38])[N:9]=2)=[CH:4][CH:3]=1.F.C(=O)(O)[O-].[Na+]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16](=[O:32])[CH2:17][C@@H:18]([OH:24])[CH2:19][C:20]([O:22][CH3:23])=[O:21])=[C:12]([CH:33]([CH3:35])[CH3:34])[N:11]=[C:10]([N:36]([CH3:41])[S:37]([CH3:40])(=[O:39])=[O:38])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 22848604Methyl (3R,6E)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-5-oxo-6-heptenoate

Product 1

HCID 22848603Methyl (3R,6E)-7-[4-(4-fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3-hydroxy-5-oxo-6-heptenoateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 16 g of the compound 6 in 100 ml of acetonitrile is added dropwise a solution of 48% hydrogen flouride in 400 ml of acetonitrile (1:19) under ice-cooling, and the mixture is warmed to room temperature and stirred for 1.5 hours. The reaction mixture is neutralized with sodium bicarbonate and extracted with ether. The organic layer is washed with sodium chloride, dried and evaporated under reduced pressure to distil ether to give 13 g (Yield: 100%) of methyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-(3R)-3-hydroxy-5-oxo-(E)-6-heptenate 7 as syrup.

Workup

  1. temperaturecooling
  2. extractionextracted with ether
  3. washThe organic layer is washed with sodium chloride
  4. customdried
  5. customevaporated under reduced pressure
  6. customto distil ether

Sources & evidence

ORD record
ord-cddc595e00a2409894c2cb98b9e44764
Source dataset
uspto-grants-2001_08
Patent number
USRE037314E1

Reaction notes

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