Diethyl 2-benzylpropanedioate → HCID 21848238, compound

HRID 862040Notes

Reaction equation

HRID 862040 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[CH2:17]([CH:24]([C:30](OCC)=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:12]([O:11][P:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:30]([CH:24]([CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:31])=[CH:16][CH:15]=1)([O:8][CH2:9][CH3:10])=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 69090Diethyl 2-benzylpropanedioateHCID 88358Diethyl p-aminobenzylphosphonate

Product 1

HCID 21848238HCID 21848238, compoundYield 45.1%

Conditions

Temperature
160 °C

Procedure

A mixture of diethyl 4-aminobenzylphosphonate (10 g) and diethyl benzylmalonate (24 g) was stirred at 160° C. for 24 hours. After cooling, the reaction mixture was purified by column chromatography on silica gel. Elution with chloroform-methanol (100:1, v/v) gave ethyl 2-(p-diethoxyphosphorylmethylphenylaminocarbonyl)-3-phenylpropionate (8.3 g, 45%) as crystals. Recrystallization from ethyl acetate-hexane gave colorless crystals having melting point of 115° to 116° C.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was purified by column chromatography on silica gel
  3. washElution with chloroform-methanol (100:1

Sources & evidence

ORD record
ord-edadab8f07a5481da85f0b14d85c840c
Source dataset
uspto-grants-1998_02
Patent number
US05716980

Reaction notes

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