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

HRID 17986Notes

Reaction equation

HRID 17986 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.[C:18](OCC)(=[O:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[CH2:22]([O:21][C:19](=[O:20])[C:18]([NH:9][CH2:8][C:7]([O:6][CH2:2][CH2:3][CH2:4][CH3:5])=[O:10])=[O:24])[CH3:23]

Participants

5

Reactant 3

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

Product 1

HCID 69643286butyl N-[ethoxy(oxo)acetyl]glycinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-butoxy-2-oxoethanaminium chloride (573.5 g, 3.42 mol), triethylamine (415 g, 4.1 mol), and diethyl oxalate (1.0 kg, 6.8 mol) in ethanol (7 L) was heated at 50° C. for 3 hours. The product mixture was cooled and concentrated under vacuum. The residue was dissolved in methylene chloride and washed with two 4 L portions of water. The organic fraction was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residual oil was subjected to column chromatography on silica gel eluting with heptane/ethyl acetate gradient. Collection and concentration of appropriate fractions provided the title material.

Workup

  1. temperatureThe product mixture was cooled
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in methylene chloride
  4. washwashed with two 4 L portions of water
  5. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-fa07b4791c9b48b1be3f24bcac22d158
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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