Sodium Chloride → Trandolapril

HRID 2242532

Reaktionsgleichung

Reaktionsgleichung von HRID 2242532
[CH2:1]([O:3][C:4]([CH:6]([NH:15][C@H:16]([C:18]([OH:20])=O)[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].[NH:21]1[C@@H:29]2[C@H:24]([CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:23][C@H:22]1[C:30]([OH:32])=[O:31].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Na+].[Cl-]>C(#N)C.CN(C=O)C.C(N(CC)CC)C>[CH3:2][CH2:1][O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([N:21]1[C@H:22]([C:30]([OH:32])=[O:31])[CH2:23][C@@H:24]2[C@@H:29]1[CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:20])[CH3:17])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5]

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7018901(2S,3aR,7aS)-Octahydro-1H-indole-2-carboxylic acidHCID 13044262N-(1-ethoxycarbonyl-3-phenylpropyl)-L-alanine

Produkt 1

HCID 5484727TrandolaprilAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To 2.79 g of (S)-1-(N-(1-(ethoxycarbonyl)-3-phenylpropyl)-L-alanine and 1.75 g of (2S,3aR,7aS)-octahydro-1H-indol-2-carboxylic acid in 100 ml of acetonitrile and 5 ml DMF first 2.9 ml of triethylamine and then with stirring 3.8 g O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate were and the stirring of the mixture was continued for 30 minutes at room temperature. Finally, 300 ml of saturated NaCl solution was added and the mixture was extracted twice with 100 ml of ethyl acetate. After isolation of the product, which was done by the same way as in example 1, 3.96 g (92%) of trandolapril was obtained.

Aufarbeitung

  1. extractionthe mixture was extracted twice with 100 ml of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ea87d675a8b64bf4ac30b3d92c8d90c9
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07671215B2

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