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N,N-Dimethylacrylamide → 1alpha,3beta-bis(tert-butyldimethylsilyloxy)-17-(N,N-dimethylaminocarbonylethoxymethyl)androsta-5,7,16-triene

HRID 1014972
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HRID 1014972 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][OH:29])[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].[CH3:38][N:39]([CH3:44])[C:40](=[O:43])[CH:41]=[CH2:42].[H-].[Na+]>O1CCCC1>[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:29][CH2:42][CH2:41][C:40]([N:39]([CH3:44])[CH3:38])=[O:43])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 17587N,N-DimethylacrylamideHCID 24758Sodium hydrideHCID 673014381alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene

생성물 1

HCID 673012321alpha,3beta-bis(tert-butyldimethylsilyloxy)-17-(N,N-dimethylaminocarbonylethoxymethyl)androsta-5,7,16-triene수율 93.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

1α,3β-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (951 mg, 1.75 mmol) was treated with N,N-dimethylacrylamide (540 mg, 5.44 mmol) and sodium hydride (60% in oil, 105 mg, 2.62 mmol) in tetrahydrofuran (17.5 ml) in the same manner as shown in Example 4(1) (at 5° C. for 14 hours), followed by work up and purification using column chromatography (hexane:ethyl acetate= 2:1) to give the titled compound (1.05 g, 92.7%) as a yellow oil.

후처리

  1. customas shown in Example 4(1) (at 5° C. for 14 hours)
  2. custompurification

출처 및 근거

ORD 기록
ord-b6806523fd05424d94c51e6cad121bc5
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07985744B2

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