Triethylamine → 17-Acetylthiomethyl-1alpha,3beta-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene

HRID 1014966노트

반응식

HRID 1014966 반응식
[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28]O)[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[C:50]([O-:53])(=[S:52])[CH3:51].[K+]>O1CCCC1.CS(C)=O.CCCCCC>[C:50]([S:52][CH2:28][C:20]1[C@:21]2([CH2:23][CH2:24][C@H:25]3[C:16](=[CH:15][CH:14]=[C:13]4[C@:26]3([CH3:27])[C@@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[CH2:10][C@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:12]4)[C@@H:17]2[CH2:18][CH:19]=1)[CH3:22])(=[O:53])[CH3:51]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23670855Potassium ethanethioateHCID 673014381alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene

생성물 1

HCID 8658997017-Acetylthiomethyl-1alpha,3beta-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene수율 88.3%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (4.00 g, 7.34 mmol) in tetrahydrofuran (70 ml), triethylamine (4.10 ml, 29.4 mmol) was added and methanesulfonyl chloride (1.70 ml, 22.0 mmol) was further added dropwise at −10° C., followed by stirring for 20 minutes. After warming to room temperature, a solution of potassium thioacetate (3.73 g, 29.4 mmol) in dimethyl sulfoxide (70 ml) was added to the reaction mixture. The reaction mixture was stirred for 30 minutes, diluted with hexane, washed with water and then dried over anhydrous magnesium sulfate. After evaporation under reduced pressure to remove the solvent, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give the titled compound (3.91 g, 88%) as a colorless oil.

후처리

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter evaporation under reduced pressure
  5. customto remove the solvent
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

출처 및 근거

ORD 기록
ord-5332aaacd798420fbad39b74a8fc728b
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985744B2

반응 노트

불러오는 중…