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Water → 2-(Acetylamino)-2-[[3-methoxy-2-(phenylmethoxy)phenyl]methyl]-propanedioic acid, diethyl ester

HRID 5902
Notes
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Reaction equation

HRID 5902 reaction equation
[O-]CC.[Na+].[C:5]([NH:8][CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6].Cl[CH2:21][C:22]1[C:23]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:24]([O:28][CH3:29])[CH:25]=[CH:26][CH:27]=1.O>C(O)C.C(O)(=O)C>[C:5]([NH:8][C:9]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:23]=1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:7])[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxideHCID 224024543-(Chloromethyl)-2-phenylmethoxyanisole

Product 1

HCID 1317181682-(Acetylamino)-2-[[3-methoxy-2-(phenylmethoxy)phenyl]methyl]-propanedioic acid, diethyl esterYield 66.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent
HCID 702EthanolSolvent3×

Procedure

A quantity of 136.20 g (0.42 mole) of 21 wt.% sodium ethoxide in ethanol is added to a stirred solution of 90.14 g (0.415 mole) of diethyl acetamidomalonate (Aldrich) in 800 mL of absolute ethanol. A solution of the benzyl chloride derivative of Example 38 in 500 mL of absolute ethanol is added and the mixture is heated at reflux for 2 hours. The cooled mixture is poured into 4 L of ice and water containing 20.0 g of glacial acetic acid. The supernatant is decanted from the separated gum. The gum is dissolved in 2 L of ether, the solution dried (magnesium sulfate), and concentrated to ca 300 mL volume. Petroleum ether (100 mL) is added to precipitate 107.1 g (66.4% yield) of pure crystalline product; mp 94°-96° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2 hours
  3. customThe supernatant is decanted from the separated gum
  4. dissolutionThe gum is dissolved in 2 L of ether
  5. dry with materialthe solution dried (magnesium sulfate)
  6. concentrationconcentrated to ca 300 mL volume

Sources & evidence

ORD record
ord-f93f0562c268458cb7f1687b9cb17055
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05246943

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes