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 990080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990080
[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

Komponenten

6

Edukt 3

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

Produkt 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-propanolAusbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-34a2e239ea4845b3872260d08bfb8cc4
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458817B1

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