Diethyl Oxalate → butyl N-[ethoxy(oxo)acetyl]glycinate

HRID 1817327Notes

Reaction equation

HRID 1817327 reaction equation
[Cl-].[CH2:2]([O:6][C:7](=[O:10])[CH2:8][NH3+:9])[CH2:3][CH2:4][CH3:5].C(N(CC)CC)C.[CH2:18]([O:20][C:21](=[O:27])[C:22](OCC)=[O:23])[CH3:19]>C(O)C>[CH2:18]([O:20][C:21](=[O:27])[C:22]([NH:9][CH2:8][C:7]([O:6][CH2:2][CH2:3][CH2:4][CH3:5])=[O:10])=[O:23])[CH3:19]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 8471TriethylamineHCID 133112781(2-Butoxy-2-oxoethyl)azanium chloride

Product 1

HCID 69643286butyl N-[ethoxy(oxo)acetyl]glycinateYield 151.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

2-Butoxy-2-oxoethanaminium chloride (573.5 g, 3.42 mol) was suspended in 7 L of ethanol and triethylamine (415 g, 4.1 mol) was added. Diethyloxalate (1.0 Kg, 6.8 mol) was added and the reaction warmed to 50° C. for 3 hours. The reaction was cooled, the volatiles were removed under vacuum and the residue was dissolved in methylene chloride and washed with two 4 L portions of water and dried over MgSO4. The next day the reaction was filtered, evaporated to give ˜1.2 Kg of an oil that was chromatographed on silica eluting with Heptane/EtOAc to give product.

Workup

  1. temperatureThe reaction was cooled
  2. customthe volatiles were removed under vacuum
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with two 4 L portions of water
  5. dry with materialdried over MgSO4
  6. filtrationThe next day the reaction was filtered
  7. customevaporated

Sources & evidence

ORD record
ord-a25d40454cc741eaa88fe60f6c0ebda2
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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