Acetamidomalonic acid diethyl ester → HCID 3120443, compound

HRID 1425918Notes

Reaction equation

HRID 1425918 reaction equation
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].[F:17][C:18]([F:28])([F:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.[Br-].[Na+]>C(O)C>[C:2]([NH:5][C:6]([CH2:23][C:22]1[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:27])[F:28])=[CH:26][CH:25]=1)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3]

Participants

6

Reactant 4

HCID 14041Acetamidomalonic acid diethyl esterHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 253881Sodium BromideHCID 5360545Sodium

Product 1

HCID 3120443HCID 3120443, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium metal (2.9 g; 0.125 mol) in absolute ethanol (500 mL) was added diethyl acetamidomalonate (LX) (27.2 g, 0.125 mol) followed by 4-(trifluoromethyl)benzyl bromide (LXI) (29.9 g, 0.125 mol). The reaction mixture was stirred at reflux overnight, during which time substantial amount of sodium bromide precipitated. The reaction mixture was concentrated to ca. 30% of its initial volume under reduced pressure and poured into cold water (400 mL). The precipitate was filtered and washed with water (3×250 mL), hexanes (3×150 mL) and then air dried to yield diethyl 2-acetamido-2-(4-(trifluoromethyl)benzyl)malonate (LXII) as a white solid used directly for the next step.

Workup

  1. customprecipitated
  2. concentrationThe reaction mixture was concentrated to ca. 30% of its initial volume under reduced pressure
  3. additionpoured into cold water (400 mL)
  4. filtrationThe precipitate was filtered
  5. washwashed with water (3×250 mL), hexanes (3×150 mL)
  6. customair dried

Sources & evidence

ORD record
ord-a104109368384f4fae5a12fac7718814
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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