HCID 86701275, Verbindung → HCID 86701274, Verbindung

HRID 2276075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2276075
[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16]/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[O:13][CH2:12][C@H:11]([NH:24][C:25](=[O:35])[C:26]2[C:31]([OH:32])=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][N:27]=2)[C:10](=[O:36])[O:9][C@H:8]1[CH3:37])(=[O:5])[CH:2]([CH3:4])[CH3:3]>CCOC(C)=O.[Pd]>[C:1]([O:6][C@@H:7]1[C@@H:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[O:13][CH2:12][C@H:11]([NH:24][C:25](=[O:35])[C:26]2[C:31]([OH:32])=[C:30]([O:33][CH3:34])[CH:29]=[CH:28][N:27]=2)[C:10](=[O:36])[O:9][C@H:8]1[CH3:37])(=[O:5])[CH:2]([CH3:4])[CH3:3]

Komponenten

4

Edukt 1

HCID 86701275HCID 86701275, Verbindung

Produkt 1

HCID 86701274HCID 86701274, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(3S,6S,7R,8R)-8-((E)-hept-2-enyl)-3-(3-hydroxy-4-methoxypicolinamido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (163 mg, 0.31 mmol) was dissolved in EtOAc (15 mL) and passed through an H-Cube® Continuous Flow hydrogenator equipped with a 10% Pd/C cartridge (full H2, 80° C., 1 mL/min flow rate). The resulting solution was concentrated in vacuo to give the title compound (162 mg, 99%) as a white solid: mp 131-134° C.; IR (neat) 3341, 1739, 1654, 1141 cm−1; 1H NMR (400 MHz, CDCl3) δ 11.81 (s, 1H), 8.66 (d, J=8.1 Hz, 1H), 8.01 (d, J=5.2 Hz, 1H), 6.89 (d, J=5.2 Hz, 1H), 5.19 (m, 1H), 5.14-5.02 (m, 1H), 5.02-4.87 (m, 1H), 3.95 (s, 3H), 3.87-3.69 (m, 1H), 2.70-2.52 (m, 2H), 1.80-1.66 (m, 1H), 1.43-1.08 (m, 21H), 0.86 (t, J=6.8 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 175.59, 172.71, 169.77, 169.00, 155.47, 148.87, 140.74, 129.98, 109.74, 75.20, 74.94, 65.12, 56.16, 50.07, 34.13, 31.70, 29.25, 28.98, 28.40, 27.09, 22.62, 18.98, 18.97, 17.82, 14.08; ESIMS m/z 523.4 ([M+H]+).

Aufarbeitung

  1. concentrationThe resulting solution was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2a929b662123440a8e219226c08f5627
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09131690B2

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