홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Acetyl chloride → 3-Acetoxy-1-benzhydryl-3-[(3,5-difluorophenyl)(methylsulfonyl)methyl]azetidine

HRID 18069
노트
인쇄 미리보기

반응식

HRID 18069 반응식
N1CCC1.C([Li])CCC.[CH3:10][S:11]([CH2:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=1)(=[O:13])=[O:12].[CH:23]([N:36]1[CH2:39][C:38](=[O:40])[CH2:37]1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:41](Cl)(=[O:43])[CH3:42]>CCCCCC.O1CCCC1.ClCCl.C(O)C.O>[C:41]([O:40][C:38]1([CH:14]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([F:22])[CH:16]=2)[S:11]([CH3:10])(=[O:12])=[O:13])[CH2:39][N:36]([CH:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:37]1)(=[O:43])[CH3:42]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

11

반응물 5

HCID 6367Acetyl chlorideHCID 10422AzetidineHCID 27614353,5-DifluorobenzylmethylsulfoneHCID 37355581-(Diphenylmethyl)azetidin-3-oneHCID 178418339Butyllithium

생성물 1

HCID 225067243-Acetoxy-1-benzhydryl-3-[(3,5-difluorophenyl)(methylsulfonyl)methyl]azetidine

시약·촉매·용매

5
HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-30 °C

실험 절차

3-Acetoxy-1-benzhydryl-3-[(3,5-difluoro-phenyl)methylsulfonyl)methyl]azetidine may be prepared may be prepared in the following manner: 47.1 cm3 of 1.6 N n-butyllithium in solution in hexane are added dropwise over approximately 25 minutes to a suspension of 12.37 g of 3,5-difluorobenzyl methyl sulfone in 200 cm3 of tetrahydrofuran, under an inert nitrogen atmosphere at a temperature in the region of −30° C. The cloudy yellow solution is stirred at a temperature in the region of −30° C. for 2 hours and then a solution of 11.87 g of 1-benzhydrylazetidin-3-one in 75 cm3 of dichloromethane is added dropwise. The reaction mixture is stirred for 1.5 hours at a temperature in the region of −30° C. and then 6.07 cm3 of acetyl chloride are added and the temperature of the medium is allowed to return to a temperature in the region of −10° C. over about 30 minutes. 200 cm3 of water and 100 cm3 of dichloromethane are added. After stirring vigorously for 30 minutes and decantation, the organic phase is washed with 3 times 150 cm3 of a saturated aqueous sodium hydrogen carbonate solution, 150 cm3 of a saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The crystalline residue obtained is taken up in 50 cm3 of boiling ethanol. The white suspension obtained is allowed to stand overnight at a temperature in the region of 20° C. and then the solid obtained is drained over sintered glass, rinsed with diisopropyl ether and dried under reduced pressure at a temperature in the region of 50° C. 19.5 g of 3-acetoxy-1-benzhydryl-3-[(3,5-difluorophenyl)(methyl-sulfonyl)methyl]azetidine are thus obtained in the form of white crystals.

후처리

  1. custombe prepared in the following manner
  2. stirringThe reaction mixture is stirred for 1.5 hours at a temperature in the region of −30° C.
  3. waitto return to a temperature in the region of −10° C. over about 30 minutes
  4. stirringAfter stirring vigorously for 30 minutes
  5. washdecantation, the organic phase is washed with 3 times 150 cm3 of a saturated aqueous sodium hydrogen carbonate solution, 150 cm3 of a saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customThe crystalline residue obtained
  10. customThe white suspension obtained
  11. waitto stand overnight at a temperature in the region of 20° C.
  12. customthe solid obtained
  13. washrinsed with diisopropyl ether
  14. customdried under reduced pressure at a temperature in the region of 50° C

출처 및 근거

ORD 기록
ord-9027c4a2bcb94de2a90d82ebc0460ef9
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07741316B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트