Acetyl chloride → HCID 86701334, Verbindung

HRID 2283024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2283024
[F:1][C:2]1[CH:39]=[CH:38][C:5]([O:6][C@@H:7]2[C@@H:15]([O:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C@H:14]([CH3:24])[O:13][C:12](=[O:25])[C@@H:11]([NH:26][C:27](=[O:37])[C:28]3[C:33]([OH:34])=[C:32]([O:35][CH3:36])[CH:31]=[CH:30][N:29]=3)[CH2:10][O:9][CH2:8]2)=[CH:4][CH:3]=1.[C:40](Cl)(=[O:42])[CH3:41]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:40]([O:34][C:33]1[C:28]([C:27](=[O:37])[NH:26][C@H:11]2[CH2:10][O:9][CH2:8][C@H:7]([O:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:39][CH:38]=3)[C@@H:15]([O:16][C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[C@H:14]([CH3:24])[O:13][C:12]2=[O:25])=[N:29][CH:30]=[CH:31][C:32]=1[O:35][CH3:36])(=[O:42])[CH3:41]

Komponenten

5

Edukt 2

HCID 6367Acetyl chlorideHCID 86701335N-((3S,7S,8S,9S)-7,8-bis(4-fluorophenoxy)-9-methyl-2-oxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide

Produkt 1

HCID 86701334HCID 86701334, VerbindungAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of N-((3S,7S,8S,9S)-7,8-bis(4-fluorophenoxy)-9-methyl-2-oxo-1,5-dioxonan-3-yl)-3-hydroxy-4-methoxypicolinamide (54 mg, 0.099 mmol) in DCM (0.5 mL) was added TEA (0.028 mL, 0.198 mmol), DMAP (6.1 mg, 0.050 mmol), and acetyl chloride (0.011 ml, 0.149 mmol). The reaction was warmed to 40° C. for and stirred for 14 h. The reaction was then concentrated and the crude residue purified by flash chromatography (SiO2, EtOAc/Hexanes) to give the title compound as a white foam (46.5 mg, 80%): IR (thin film) 3372, 2939, 1765, 1676 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.78 (d, J=8.2 Hz, 1H), 8.37 (d, J=5.4 Hz, 1H), 7.03 (d, J=5.5 Hz, 1H), 6.98-6.86 (m, 6H), 6.74-6.61 (m, 2H), 5.33-5.24 (m, 1H), 5.14 (m, 1H), 4.36 (t, J=9.2 Hz, 1H), 4.30-4.22 (m, 1H), 4.10-3.99 (m, 2H), 3.92 (s, 3H), 3.92-3.87 (m, 1H), 3.79 (dd, J=11.2, 7.3 Hz, 1H), 2.40 (s, 3H), 1.48 (d, J=6.4 Hz, 3H); HRMS-FAB (m/z) [M+H]+ calcd for C29H28F2N2O9, 587.1836; found, 587.1838.

Aufarbeitung

  1. concentrationThe reaction was then concentrated
  2. customthe crude residue purified by flash chromatography (SiO2, EtOAc/Hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ecf5102c58284a6e982db6aed4cf8c97
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09144239B2

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