Isoamyl Nitrite → 2-(R)-(4-Acetoxymethyl-1H-indazol-5-ylmethyl)-succinic acid diethyl ester

HRID 132426

Reaktionsgleichung

Reaktionsgleichung von HRID 132426
[N:1](OCCC(C)C)=O.[CH2:9]([O:11][C:12](=[O:34])[C@H:13]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([CH3:28])[C:22]=1[CH2:29][O:30][C:31](=[O:33])[CH3:32])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:10]>C(O)(=O)C.C(Cl)(Cl)Cl.ClCCl>[CH2:9]([O:11][C:12](=[O:34])[C@H:13]([CH2:20][C:21]1[C:22]([CH2:29][O:30][C:31](=[O:33])[CH3:32])=[C:23]2[C:24](=[CH:25][CH:26]=1)[NH:27][N:1]=[CH:28]2)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:10]

Komponenten

5

Edukt 2

HCID 8053Isoamyl NitriteHCID 597320262-(R)-(2-Acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl ester

Produkt 1

HCID 597318982-(R)-(4-Acetoxymethyl-1H-indazol-5-ylmethyl)-succinic acid diethyl esterAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21584526Acetic acid chloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Isoamyl nitrite (170 μL, 1.3 mmol) was added dropwise to a cooled (water ice bath) solution of 2-(R)-(2-acetoxymethyl-4-amino-3-methyl-benzyl)-succinic acid diethyl ester in 5% acetic acid—chloroform (5 mL). Mixture was stirred at 0° C. for 1.5 hours. Mixture was diluted with dichloromethane (20 mL) and then washed with saturated aqueous sodium bicarbonate (2×20 mL). Organic was dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained as amber oil in 99% yield. MS m/e (M+H)+=377.1.

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate (2×20 mL)
  2. dry with materialOrganic was dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-328a05757f1c486d8af0c87bcc1c2e92
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384931B2

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