(3,4-Dichlorophenyl)methanesulfonyl chloride → 17-cyclopropylmethyl-3-tert-butyldimethylsilyloxy-14beta-hydroxy-4,5alpha-epoxy-6alpha-(N-methyl-3,4-dichlorophenylmethanesulfonamido)morphinan

HRID 567433

반응식

HRID 567433 반응식
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:26]([CH2:27][CH:28]4[CH2:30][CH2:29]4)[CH2:25][CH2:24][C@:20]45[C:21]=2[C:22]=1[O:23][C@H:19]4[C@@H:18]([NH:31][CH3:32])[CH2:17][CH2:16][C@@:15]35[OH:33])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:34][C:35]1[CH:36]=[C:37]([CH2:42][S:43](Cl)(=[O:45])=[O:44])[CH:38]=[CH:39][C:40]=1[Cl:41]>N1C=CC=CC=1>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:26]([CH2:27][CH:28]4[CH2:29][CH2:30]4)[CH2:25][CH2:24][C@:20]45[C:21]=2[C:22]=1[O:23][C@H:19]4[C@@H:18]([N:31]([CH3:32])[S:43]([CH2:42][C:37]1[CH:38]=[CH:39][C:40]([Cl:41])=[C:35]([Cl:34])[CH:36]=1)(=[O:45])=[O:44])[CH2:17][CH2:16][C@@:15]35[OH:33])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 2794622(3,4-Dichlorophenyl)methanesulfonyl chlorideHCID 5380405917-Cyclopropylmethyl-3-tert-butyldimethylsilyloxy-14beta-hydroxy-4,5alpha-epoxy-6alpha-methylaminomorphinan

생성물 1

HCID 9122191517-cyclopropylmethyl-3-tert-butyldimethylsilyloxy-14beta-hydroxy-4,5alpha-epoxy-6alpha-(N-methyl-3,4-dichlorophenylmethanesulfonamido)morphinan수율 78.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

203.9 mg of 3-tert-butyldimethylsilyloxy-17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxy-6α-methylaminomorphinan 7 obtained in reference example 5 was dissolved in 3 ml of pyridine followed by the addition of 124 mg of 3,4-dichorophenylmethanesufonylchloride and stirring for 30 minutes at room temperature. After concentrating the reaction system, 3 ml of saturated aqueous sodium bicarbonate and 3 ml of chloroform were added to separate layers, after which the aqueous layer was extracted twice with 3 ml of chloroform. After drying with anhydrous sodium sulfate, the organic layer was concentrated to obtain the oily crude product. This was then purified with silica gel column chromatography (30 g benzene/ethyl acetate=5/1) to obtain 235.4 mg of the target compound (yield: 78%).

후처리

  1. concentrationAfter concentrating the reaction system, 3 ml of saturated aqueous sodium bicarbonate and 3 ml of chloroform
  2. additionwere added
  3. customto separate layers
  4. extractionafter which the aqueous layer was extracted twice with 3 ml of chloroform
  5. dry with materialAfter drying with anhydrous sodium sulfate
  6. concentrationthe organic layer was concentrated
  7. customto obtain the oily crude product
  8. customThis was then purified with silica gel column chromatography (30 g benzene/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-0b86d96cb9e841e78af2563a0e2536f8
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177438B1

연결된 노트

불러오는 중…