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Potassium Carbonate → (R)-1-(4-benzyloxy-3,5-dimethyl-benzyl)-2-(1'-ethoxycarbonylmethyl-4,4'-bipiperidinyl-1-yl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 599760
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 599760
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH3:2].[O:19]=[C:20]1[N:26]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C@@H:36]([C:54](O)=[O:55])[CH2:37][C:38]3[CH:43]=[C:42]([CH3:44])[C:41]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[C:40]([CH3:53])[CH:39]=3)=[O:34])[CH2:29][CH2:28]2)[CH2:25][CH2:24][C:23]2[CH:57]=[CH:58][CH:59]=[CH:60][C:22]=2[NH:21]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CN(C=O)C>[O:19]=[C:20]1[N:26]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C@H:36]([CH2:37][C:38]3[CH:43]=[C:42]([CH3:44])[C:41]([O:45][CH2:46][C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)=[C:40]([CH3:53])[CH:39]=3)[C:54]([N:15]3[CH2:16][CH2:17][CH:12]([CH:9]4[CH2:8][CH2:7][N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18])[CH2:11][CH2:10]4)[CH2:13][CH2:14]3)=[O:55])=[O:34])[CH2:29][CH2:28]2)[CH2:25][CH2:24][C:23]2[CH:57]=[CH:58][CH:59]=[CH:60][C:22]=2[NH:21]1
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Komponenten

8

Edukt 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22945803Ethyl[4,4']bipiperidinyl-1-yl-acetateHCID 25208036(R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Produkt 1

HCID 67273836(R)-1-(4-benzyloxy-3,5-dimethyl-benzyl)-2-(1'-ethoxycarbonylmethyl-4,4'-bipiperidinyl-1-yl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.99 g (3.90 mmol) ethyl[4,4′]bipiperidinyl-1-yl-acetate were added at RT to a solution of 2.00 g (3.50 mmol) (R)-2-(4-benzyloxy-3,5-dimethyl-phenyl)-1-carboxy-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate (Example 1g), 1.25 g (3.90 mmol) TBTU and 0.67 mL (3.90 mmol) ethyldiisopropylamine in 20 mL THF and 5 mL DMF and the reaction mixture was stirred overnight. 15% K2CO3 solution was added, the mixture was extracted exhaustively with EtOAc, the combined organic phases were washed with saturated NaCl solution and dried on Na2SO4. After the elimination of the desiccant and solvent the product was obtained, which was reacted further without purification.

Aufarbeitung

  1. extractionthe mixture was extracted exhaustively with EtOAc
  2. washthe combined organic phases were washed with saturated NaCl solution
  3. customdried on Na2SO4
  4. customAfter the elimination of the desiccant and solvent the product was obtained
  5. customwhich was reacted further without purification

Quellen und Nachweise

ORD-Eintrag
ord-21606aebcd264c69a086e43637dd8002
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897603B2

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