4-({[5-(Tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethylamine → (2S)-1-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-3-{[4-({[5-(tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-2-propanol

HRID 990075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 990075
[C:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][S:11]([C:14]2[CH:22]=[CH:21][C:17]([CH2:18][CH2:19][NH2:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:23]([Si:27]([O:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][C@@H:49]2[CH2:51][O:50]2)=[CH:43][CH:42]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH3:26])([CH3:25])[CH3:24].ClCCl.C(Cl)(Cl)Cl.CO>CO.C1COCC1>[Si:27]([O:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][C@@H:49]([OH:50])[CH2:51][NH:20][CH2:19][CH2:18][C:17]2[CH:16]=[CH:15][C:14]([S:11]([CH2:10][C:7]3[N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[O:9][N:8]=3)(=[O:13])=[O:12])=[CH:22][CH:21]=2)=[CH:43][CH:42]=1)([C:23]([CH3:24])([CH3:26])[CH3:25])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Komponenten

6

Edukt 3

HCID 113133214-({[5-(Tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethylamineHCID 11327180t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilaneHCID 86584582Dichloromethane chloroform methanol

Produkt 1

HCID 11456872(2S)-1-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-3-{[4-({[5-(tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-2-propanolAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of the amine of Example 13 (0.873 g, 2.70 mmol) and tert-butyl{4-[(2S)oxiranylmethoxy]phenoxy}diphenylsilane (0.980 g, 2.42 mmol) in a mixture of methanol (20 mL) and THF (3 mL) was heated to 45° C. for 23 h. TLC shows characteristic product spot at Rf=0.25(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 0.660 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-c80d0b3e66c94473a630c65d80e0749d
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06458817B1

Notizen zur Reaktion

Wird geladen…