Malonic Acid → β-Amino-3,5-bis(1,1-dimethylethyl)benzenepropanoic acid

HRID 1526780Notes

Reaction equation

HRID 1526780 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[C:17]([OH:23])(=[O:22])[CH2:18]C(O)=O.C([O-])(=O)C.[NH4+:28]>C(O)(C)C>[NH2:28][CH:8]([C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=1)[CH2:18][C:17]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 517165Ammonium AcetateHCID 12682533,5-Bis(tert-butyl)benzaldehyde

Product 1

HCID 86709945β-Amino-3,5-bis(1,1-dimethylethyl)benzenepropanoic acidYield 26.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture 3,5-di-tert-butylbenzaldehyde (0.996 g, 4.56 mmol), malonic acid (0.572 g, 5.50 mmol) and ammonium acetate (0.710 g, 9.21 mmol) in isopropanol (30 mL) was heated at reflux under nitrogen for 5 h to afford a colorless solid. The solid was filtered and washed with hot isopropanol (30 mL). The residue was dried in vacuo to give the desired racemic product as a colorless solid (0.340 g).

Workup

  1. temperatureat reflux under nitrogen for 5 h
  2. customto afford a colorless solid
  3. filtrationThe solid was filtered
  4. washwashed with hot isopropanol (30 mL)
  5. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-ce84743ee1ef480bac7b84cb91043257
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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