Acetic Acid → HCID 15618374, compound

HRID 345354Notes

Reaction equation

HRID 345354 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:8][CH2:9][C:10](OCC)=[O:11])=[O:5])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[K+].C(O)(=O)C.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH2:18]([O:17][C:15]([N:7]1[CH2:8][CH2:9][C:10](=[O:11])[CH:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:16])[CH3:19]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24243Trisodium PhosphateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 4381617ethyl 3-[ethoxycarbonyl-(2-ethoxy-2-oxoethyl)amino]propanoate

Product 1

HCID 15618374HCID 15618374, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 53.9 g of ethyl N-(ethoxycarbonylmethyl)-N-(ethoxycarbonyl)-β-alaninate in 200 ml of toluene is added dropwise to a stirred solution of potassium hexamethyldisilazide (429 ml, 0,653 M) in 125 ml of toluene under nitrogen and cooled to 0° . After 45 minutes at 0°, 21.6 ml of acetic acid is added followed by a solution of 100 g of sodium phosphate (monobasic) in 1 liter of water. The layers are separated, the organic layer is washed with pH 7 buffer, dried over sodium sulfate, filtered, concentrated and purified by flash chromatography using ethyl acetate/hexane (3:7) to yield ethyl 1-ethoxycarbonyl-3-oxo-pyrrolidine-2-carboxylate.

Workup

  1. temperaturecooled to 0°
  2. customThe layers are separated
  3. washthe organic layer is washed with pH 7 buffer
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e46a9b69046746968d35b8b36491fd6e
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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