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 990080ノート

反応式

HRID 990080 の反応式
[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

参加物

6

反応物 3

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

生成物 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-propanol収率 41.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-34a2e239ea4845b3872260d08bfb8cc4
出典データセット
uspto-grants-2002_10
特許番号
US06458817B1

反応ノート

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