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 1177734Notes

Reaction equation

HRID 1177734 reaction equation
[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

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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)+.

Workup

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

Sources & evidence

ORD record
ord-b21808d5f66549d998f50eaa8bc8feca
Source dataset
uspto-grants-2010_11
Patent number
US07842808B2

Reaction notes

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