Hydrofluoric Acid → (R,E)-Methyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate

HRID 649710노트

반응식

HRID 649710 반응식
[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

참가 물질

5

반응물 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 22848604(R,E)-Methyl 3-[(tert-butyldimethylsilyl)oxy]-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]-5-oxohept-6-enoate

생성물 1

HCID 22848603(R,E)-Methyl 7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methylmethylsulfonamido)pyrimidin-5-yl]-3-hydroxy-5-oxohept-6-enoate수율 100.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cddc595e00a2409894c2cb98b9e44764
출처 데이터셋
uspto-grants-2001_08
특허 번호
USRE037314E1

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