2-(1-{[2,4-Bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)acetaldehyde → cyclopentyl N-[2-(1-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-valinate

HRID 632572

Reaktionsgleichung

Reaktionsgleichung von HRID 632572
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH:35]=O)[CH2:30][CH2:29]1)=[O:27])C1C=CC=CC=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:48]1([O:53][C:54](=[O:60])[C@H:55]([CH:57]([CH3:59])[CH3:58])[NH2:56])[CH2:52][CH2:51][CH2:50][CH2:49]1>>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[C:12]([CH:23]([CH3:24])[CH3:25])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:33][CH2:32][CH:31]([CH2:34][CH2:35][NH:56][C@H:55]([C:54]([O:53][CH:48]2[CH2:49][CH2:50][CH2:51][CH2:52]2)=[O:60])[CH:57]([CH3:58])[CH3:59])[CH2:30][CH2:29]1)=[O:27]

Komponenten

3

Edukt 2

HCID 866864202-(1-{[2,4-Bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)acetaldehydeHCID 86686422L-valine cyclopentyl ester tosylate

Produkt 1

HCID 54767127cyclopentyl N-[2-(1-{[2,4-dihydroxy-5-(propan-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-valinate

Versuchsvorschrift

Prepared from Intermediate D and L-valine cyclopentyl ester tosylate. 1H NMR (300 MHz, d3-MeOD) 6.95 (1H, s), 6.34 (1H, s), 5.31-5.44 (1H, m), 4.08-4.35 (2H, m), 3.94 (1H, d, J=3.8 Hz), 3.05-3.25 (3H, m), 2.96 (2H, t, J=12.5 Hz), 2.26-2.42 (1H, m), 1.89-2.08 (3H, m), 1.61-1.88 (8H, m), 1.13-1.24 (12H, m) and 1.05 (6H, d, J=6.8 Hz) LC/MS: purity 85%, m/z 475 [M+H]+

Quellen und Nachweise

ORD-Eintrag
ord-d5d9f29874654fa881c9d768120f635d
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321718B2

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