t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilane → (2S)-1-[(4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethyl)amino]-3-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-2-propanol

HRID 990080노트

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HRID 990080 반응식
[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:24]=[CH:23][C:19]([CH2:20][CH2:21][NH2:22])=[CH:18][CH:17]=2)=[O:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([Si:29]([O:42][C:43]1[CH:48]=[CH:47][C:46]([O:49][CH2:50][C@@H:51]2[CH2:53][O:52]2)=[CH:45][CH:44]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:28])([CH3:27])[CH3:26].ClCCl.C(Cl)(Cl)Cl.CO>CO.C1COCC1>[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH2:21][NH:22][CH2:53][C@H:51]([OH:52])[CH2:50][O:49][C:46]3[CH:45]=[CH:44][C:43]([O:42][Si:29]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:48][CH:47]=3)=[CH:23][CH:24]=2)=[O:15])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 11327180t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilaneHCID 120442084-{[(5-Benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylamineHCID 86584582Dichloromethane chloroform methanol

생성물 1

HCID 12044209(2S)-1-[(4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethyl)amino]-3-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-2-propanol수율 41.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

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온도
45 °C

실험 절차

A solution of the amine of Example 22 (0.705 g, 2.00 mmol) and the epoxide of Example 9 (0.640 g, 1.594 mmol) in a mixture of methanol (25 mL) and THF (5 mL) was heated to 45° C. for 23 h. TLC shows characteristic product spot at Rf=0.2 5(silica gel plate; dichloromethane/chloroform/methanol: 20/5/2). The reaction mixture was cooled, silica gel (5 g) was added and the methanol was remove in vacuo. The reaction mixture, preabsorbed onto silica gel was applied to the top of a flash chromatography column(silica gel; dichloromethane/chloroform/methanol: 12/3/1) and purified in the standard manner. This procedure afforded 0.490 g of the title compound as a white foam.

후처리

  1. temperatureThe reaction mixture was cooled
  2. additionsilica gel (5 g) was added
  3. customthe methanol was remove in vacuo
  4. customThe reaction mixture, preabsorbed onto silica gel
  5. custompurified in the standard manner

출처 및 근거

ORD 기록
ord-34a2e239ea4845b3872260d08bfb8cc4
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458817B1

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