Malonic Acid → (RS)-beta-Amino-beta-(4-bromophenyl)propionic acid

HRID 381534Notes

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O-:13])(=[O:12])[CH3:11].[NH4+:14].C(O)(=O)CC(O)=O>C(O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([CH2:11][C:10]([OH:13])=[O:12])[NH2:14])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

4-Bromobenzaldehyde (10 g, 54 mmol), ammonium acetate (8.663 g, 112.4 mmol) and malonic acid (5.6762 g, 54.5 mmol) were refluxed (slow) in absolute ethanol (45 mL) for 150 hours. White solid was filtered and dissolved into a warm (70° C.) solution of 50 mL of Na2CO3 and 50 mL of H2O. This solution was then extracted with 100 mL of diethyl ether three times. The aqueous layer was further acidified to pH 7 to produce white solid β-4-bromophenyl-β-alanine (4.5140 g, 18.49 mmol, 34.2%); MP: 234° C.; IR (KBr): 3061, 1594 cm−1; TLC: RF=0.35 (solvent 24), 0.32 (solvent 25); 1H NMR (D2O/K2CO3): δ 7.42-7.38 (m, 2H), 7.17-7.14 (m, 2H), 4.11-4.07 (t, J=7.25 Hz, 1H), 2.48-2.36 (m, 2H). Anal. Calcd for C9H10BrNO2: C, 44.29; H, 4.13; N, 5.74. Found: C, 44.35; H, 3.93; N, 5.70.

Workup

filtrationWhite solid was filtered
dissolutiondissolved into
extractionThis solution was then extracted with 100 mL of diethyl ether three times

Sources & evidence

ORD record: ord-514402eb4e314bccad80809bffd44e79
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06306909B1

Reaction notes

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