Water → HCID 54105171, compound

HRID 843718Notes

Reaction equation

HRID 843718 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8](=[O:22])[C@H:9]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C:11]([OH:13])=[O:12])[CH:2]=1.C(=O)([O-])O.[Na+].[CH2:28](Br)[CH3:29].O>CN(C)C=O>[CH2:28]([O:12][C:11](=[O:13])[CH2:10][C@@H:9]([NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[C:8]([NH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)=[O:22])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 516892Sodium BicarbonateHCID 18734763HCID 18734763, compound

Product 1

HCID 54105171HCID 54105171, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of N-(3-pyridyl)-3(R)-(tert-butoxycarbonylamino)succinamic acid (1 g) and sodium hydrogen carbonate (0.54 g) in N,N-dimethylformamide (5 ml) was added to a solution of ethyl bromide (1.76 g) in N,N-dimethylformamide (5 ml). After stirring at room temperature for 4 days, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and brine, and dried over MgSO4, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with (CHCl3:MeOH=100:1) to give N-(3-pyridyl)-3(R)-(tert-butoxycarbonylamino)succinamic acid ethyl ester (0.63 g) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with (CHCl3:MeOH=100:1)

Sources & evidence

ORD record
ord-4d8c59a179824a77956f6c5bb78b3c22
Source dataset
uspto-grants-2002_04
Patent number
US06380215B1

Reaction notes

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