1,2-Dichloroethane → tert-butyl {2-[[(7R)-14-cyclohexyl-11-[({[(2,2-dimethoxyethyl)(methyl)amino]-sulfonyl}amino)carbonyl]-3-(pyridin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl](methyl)amino]ethyl}methylcarbamate

HRID 1669420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669420
[C:1]([O:5][C:6]([N:8]([CH3:49])[CH2:9][CH2:10][N:11]([CH3:48])[C@@H:12]1[CH2:19][N:18]2[C:20]3[CH:21]=[C:22]([C:33](O)=[O:34])[CH:23]=[CH:24][C:25]=3[C:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[C:17]2[C:16]2[CH:36]=[CH:37][C:38]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)=[CH:39][C:15]=2[O:14][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:50][O:51][CH:52]([O:60][CH3:61])[CH2:53][N:54]([CH3:59])[S:55]([NH2:58])(=[O:57])=[O:56].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:27]1([C:26]2[C:25]3[CH:24]=[CH:23][C:22]([C:33]([NH:58][S:55]([N:54]([CH2:53][CH:52]([O:51][CH3:50])[O:60][CH3:61])[CH3:59])(=[O:57])=[O:56])=[O:34])=[CH:21][C:20]=3[N:18]3[C:17]=2[C:16]2[CH:36]=[CH:37][C:38]([O:40][CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=4)=[CH:39][C:15]=2[O:14][CH2:13][C@H:12]([N:11]([CH3:48])[CH2:10][CH2:9][N:8]([CH3:49])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:19]3)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 67345446(7R)-7-[{2-[(tert-butoxycarbonyl) (methyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-3-(pyridin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acidHCID 86627889N-(2,2-dimethoxyethyl)-N-methylsulfamide

Produkt 1

HCID 67344800tert-butyl {2-[[(7R)-14-cyclohexyl-11-[({[(2,2-dimethoxyethyl)(methyl)amino]-sulfonyl}amino)carbonyl]-3-(pyridin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocin-7-yl](methyl)amino]ethyl}methylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

(7R)-7-[{2-[(tert-butoxycarbonyl)(methyl)amino]ethyl}(methyl)amino]-14-cyclohexyl-3-(pyridin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid, N-(2,2-dimethoxyethyl)-N-methylsulfamide (2 eq, see Example 1, Step 1) and DMAP (5 eq) were dissolved in DCM (24 mM) and EDC (3 eq) was added. The mixture was warmed to 40° C. After 2 h the mixture was diluted with DCM and extracted twice with H2O, sat. aq. NH4Cl and brine. The organic phase was dried over Na2SO4 and evaporated in vacuo. The product was obtained as a yellowish sticky solid and used without further purification (91%). (ES+) m/z 849 (M+H)+.

Aufarbeitung

  1. extractionextracted twice with H2O, sat. aq. NH4Cl and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe product was obtained as a yellowish sticky solid
  5. customused without further purification (91%)

Quellen und Nachweise

ORD-Eintrag
ord-47f4a846b2a5433dab73858cffeb59dc
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989438B2

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