Methyl 2-(bis((tert-butoxy)carbonyl)amino)prop-2-enoate → 2-(Di-tert-butoxycarbonylamino)-3-(7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester

HRID 2250212

Reaktionsgleichung

Reaktionsgleichung von HRID 2250212
[CH3:1][C:2]1([CH3:11])[CH2:7][NH:6][CH2:5][C:4]2[CH:8]=[N:9][NH:10][C:3]1=2.[CH3:12][O:13][C:14](=[O:32])[C:15]([N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH2:16]>CO>[CH3:12][O:13][C:14](=[O:32])[CH:15]([N:17]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:16][N:6]1[CH2:7][C:2]([CH3:11])([CH3:1])[C:3]2[NH:10][N:9]=[CH:8][C:4]=2[CH2:5]1

Komponenten

4

Edukt 2

HCID 10870342Methyl 2-(bis((tert-butoxy)carbonyl)amino)prop-2-enoateHCID 211022097,7-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

Produkt 1

HCID 588644042-(Di-tert-butoxycarbonylamino)-3-(7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl)-propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 7,7-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (160 mg) in methanol (3 mL) was added 2-(di-tert-butoxycarbonylamino)-acrylic acid methyl ester (331 mg). A gentle stream of nitrogen was applied and the reaction stirred overnight. In the morning, the volume was greatly reduced. The last traces of solvent were removed under high vacuum to give 490 mg (quant.) which was used without purification. 1H-NMR (CDCl3, 500 MHz) δ 1.24 (s, 3H), 1.26 (s, 3H), 1.38 (s, 18H), 2.33 (d, J=11.3, 1H), 2.57 (d, J=11.3, 1H), 3.09 (dd, J=13.1, 5.5, 1H), 3.15 (dd, J=13.4, 9.5, 1H), 3.35 (d, J=12.8, 1H), 3.57 (d, J=12.8, 1H), 3.68 (s, 3H), 5.13 (dd, J=9.5, 3.7, 1H), 7.16 (s, 1H). Mass spec.: 453.30 (MH)+.

Aufarbeitung

  1. customThe last traces of solvent were removed under high vacuum
  2. customto give 490 mg (quant.) which
  3. customwas used without purification

Quellen und Nachweise

ORD-Eintrag
ord-cbfc953eef1c4710900b76d32331a38b
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314883B2

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