Octanoyl chloride → HCID 71549357, Verbindung

HRID 1852359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852359
[NH2:1][C@H:2]([CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C@@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[OH:4].CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>C1COCC1.CCOC(C)=O>[OH:4][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[C@H:2]([NH:1][C:28](=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1

Komponenten

6

Edukt 3

HCID 8124Octanoyl chlorideHCID 81531DiisopropylethylamineHCID 86680953HCID 86680953, Verbindung2×

Produkt 1

HCID 71549357HCID 71549357, VerbindungAusbeute 22,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a 0° C. solution of (1R,2R)-2-amino-1-(2-methoxyphenyl)-3-(pyrrolidin-1-yl)propan-1-ol (0.1 g, 0.40 mmol) (compound 6) in THF (5 ml) was added Hunig's Base (0.07 g, 0.52 mmol), followed by the dropwise addition of octanoyl chloride (0.07 g, 0.40 mmol). The resulting mixture was allowed to stir overnight at room temperature, diluted with EtOAc, and washed with satd. aq. NaHCO3, satd. aq. NaCl, and dried over MgSO4. Purified by flash silica chromatography (MeOH/CH2Cl2) to give a yellow oil (0.03 g, 0.09 mmol, 22% yield). HPLC purity 93% (tR=5.3 min) NMR (500 MHz, CDCl3) δ 7.4 (m, 1H), 7.2-7.3 (m, 1H), 6.9-7.0 (m, 1H), 6.8-6.9 (m, 1H), 6.0-6.1 (m, 1H), 5.3 (d, 1H), 4.2-4.3 (m, 1H), 3.8 (s, 3H), 2.9-3.0 (m, 3H), 2.5-2.7 (m, 4H), 2.0-2.1 (m, 2H), 1.7-1.8 (m, 4H), 1.9-2.0 (m, 2H), 1.2-1.4 (m, 6H), 0.8-0.9 (t, 3H). ESI-MS m/z 377.2 (M+H +).

Aufarbeitung

  1. washwashed with satd
  2. dry with materialaq. NaCl, and dried over MgSO4
  3. customPurified by flash silica chromatography (MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-c6d1b963e306440e9f2c84bd315e06e8
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08961959B2

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