Acetamidomalonic acid diethyl ester → HCID 15929315, compound

HRID 542414Notes

Reaction equation

HRID 542414 reaction equation
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[CH2:16]([O:18][P:19]([CH2:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br)([O:21][CH2:22][CH3:23])=[O:20])[CH3:17]>C(O)C>[CH2:22]([O:21][P:19]([CH2:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27][C:5]([NH:4][C:1](=[O:3])[CH3:2])([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O:18][CH2:16][CH3:17])=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 14041Acetamidomalonic acid diethyl esterHCID 151719952-(Diethylphosphonomethyl)benzyl bromide

Product 1

HCID 15929315HCID 15929315, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 0.43 g (18.8 mmol) Na in 50 mL of dry ethanol was added 4.09 g (18.8 mmol) of solid diethyl acetamidomalonate portionwise. This mixture was stirred at reflux under nitrogen for 2 h, then cooled to room temperature. Then, 6.05 g (18.8 mmol) of 2-(diethylphosphonomethyl)benzyl bromide in 40 mL of ethanol was added dropwise and the mixture stirred for 24 h. The salt which precipitated was removed by filtration and the solvent concentrated at reduced pressure to yield a viscous oil. This oil was chromatographed on a column of silica gel with ethyl acetate as eluant. The combined fractions were concentrated under reduced pressure to yield 6.67 g (79%) of the product as a clear oil. IR(neat): 1745.9, 1676.5, 1501.6, 1375.6, 1247.1, 1649.1, 969.4 cm-1. 1H NMR (CDCl3) δ 1.0-1.4 (m, 12H); 2.0 (s, 3H); 2.9 (s, 1H); 3.3 (s, 1H); 3.8-4.4 (m, 10H); 5.8-7.4 (m, 5H). Anal. Calcd. for C21H32NPO8 0.5H2O: C, 54.06; H, 6.92; N, 3.00. Found: C, 53.73; H, 7.11; N, 3.27.

Workup

  1. temperatureat reflux under nitrogen for 2 h
  2. stirringthe mixture stirred for 24 h
  3. customThe salt which precipitated
  4. customwas removed by filtration
  5. concentrationthe solvent concentrated at reduced pressure
  6. customto yield a viscous oil
  7. customThis oil was chromatographed on a column of silica gel with ethyl acetate as eluant
  8. concentrationThe combined fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-995c70a5b124436187e1eba7525631b7
Source dataset
uspto-grants-1987_04
Patent number
US04657899

Reaction notes

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