Dicyclohexylcarbodiimide → 2-(2-Dodecanoylamino-3-hydroxybutanoylamino)-3-hydroxybutanoic acid

HRID 627827

Reaktionsgleichung

Reaktionsgleichung von HRID 627827
[C:1]([NH:14][CH:15]([CH:19]([OH:21])[CH3:20])[C:16]([OH:18])=O)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C[O:23][C:24](=[O:30])[CH:25]([NH2:29])[CH:26]([OH:28])[CH3:27].C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>>[C:1]([NH:14][CH:15]([CH:19]([OH:21])[CH3:20])[C:16]([NH:29][CH:25]([CH:26]([OH:28])[CH3:27])[C:24]([OH:30])=[O:23])=[O:18])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

5

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 324007Methyl 2-amino-3-hydroxybutanoateHCID 98794392-Dodecanoylamino-3-hydroxybutanoic acid

Produkt 1

HCID 231320272-(2-Dodecanoylamino-3-hydroxybutanoylamino)-3-hydroxybutanoic acidAusbeute 50,9 %

Versuchsvorschrift

2-Dodecanoylamino-3-hydroxybutanoic acid (15.07 g) and 2-amino-3-hydroxybutanoic acid methyl ester (6.66 g) were condensed with dicyclohexylcarbodiimide (10.31 g). Thereafter, methyl ester was hydrolyzed with sodium hydroxide to give 2-(2-dodecanoylamino-3-hydroxybutanoylamino)-3-hydroxybutanoic acid (10.24 g). The structure thereof was identified by 1H-NMR (400 MHz, CD3OD, r.t.).

Quellen und Nachweise

ORD-Eintrag
ord-ce3ddd5890474d97b0bb179d4da7e76c
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309486B2

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