(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol → rac-alpha-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(furan-2-yl)propionamide

HRID 275621

Reaktionsgleichung

Reaktionsgleichung von HRID 275621
C(OC([NH:11][CH:12]([CH2:16][C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)[C:13]([OH:15])=O)=O)C1C=CC=CC=1.[NH2:22][C@@H:23]([CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[C@@H:24]([OH:30])[C@H:25]([CH:27]1[CH2:29][CH2:28]1)[OH:26]>>[NH2:11][CH:12]([CH2:16][C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)[C:13]([NH:22][C@@H:23]([CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1)[C@@H:24]([OH:30])[C@H:25]([CH:27]1[CH2:29][CH2:28]1)[OH:26])=[O:15]

Komponenten

3

Edukt 2

HCID 14930738(1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediolHCID 20088483Cbz-3-(2-furyl)-DL-alanine

Produkt 1

HCID 57246147rac-alpha-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(furan-2-yl)propionamide

Versuchsvorschrift

In an analogous manner to that described above, by the condensation of (RS)-α-(1-benzyloxyformamido)-3-(furan-2-yl)propionic acid [J. Biol. Chem. 171, 383 (1947)]and (1S,2R,3S)-3-amino-4-cyclohexyl-1-cyclopropyl-1,2-butanediol followed by catalytic hydrogenation there was obtained rac-α-amino-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-3-(furan-2-yl)propionamide, MS: 365 (M+H)+, as a colourless foam.

Quellen und Nachweise

ORD-Eintrag
ord-94f259c8e7ee40429f6cefed67bda66f
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393875

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