Ethanol → 2-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-butyl-2-ethoxycarbonyl-succinic acid diethyl ester

HRID 29770Notes

Reaction equation

HRID 29770 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([CH2:17][CH2:18][CH2:19][CH3:20])[CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[H-].[Na+].[C:24]([O:28][C:29](=[O:39])[NH:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][N:32]=1)([CH3:27])([CH3:26])[CH3:25].C(O)C>CN(C=O)C.O>[CH2:10]([O:9][C:7](=[O:8])[C:6]([CH2:37][C:34]1[CH:33]=[N:32][C:31]([NH:30][C:29]([O:28][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:39])=[CH:36][CH:35]=1)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]([CH2:17][CH2:18][CH2:19][CH3:20])[C:4]([O:3][CH2:1][CH3:2])=[O:21])[CH3:11]

Participants

7

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 134450202-Butyl-3-ethoxycarbonyl-succinic acid diethyl esterHCID 23030321tert-Butyl (5-(bromomethyl)pyridin-2-yl)carbamate

Product 1

HCID 542435252-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-butyl-2-ethoxycarbonyl-succinic acid diethyl esterYield 78.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-butyl-3-ethoxycarbonyl-succinic acid diethyl ester (1 g, 3 mmol) and NaH (119 mg, 5 mmol) in DMF (20 ml) was stirred for 60 minutes at 0° C. under argon. (5-Bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.425 g, 5 mmol) was added and the mixture was stirred at room temperature for one week. Ethanol (1 ml) was added and the reaction was poured into H2O and extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The product was purified by column chromatography (heptane/ethyl acetate, 4:1 to 1:1) to give 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-butyl-2-ethoxycarbonyl-succinic acid diethyl ester (1.2 g, 71.3%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by column chromatography (heptane/ethyl acetate, 4:1 to 1:1)

Sources & evidence

ORD record
ord-54ecf76dce5245d5a20e5eab56e19121
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Reaction notes

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