Malonic Acid → 3-Amino-3-(3-cyclopentyloxy-4-methoxyphenyl)propanoic acid
Reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=2[O:15][CH3:16])[CH:10]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:17]([O-:20])(=[O:19])[CH3:18].[NH4+:21].C(O)(=O)CC(O)=O>C(O)C>[NH2:21][CH:10]([C:9]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:8]=1)[CH2:18][C:17]([OH:20])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
A stirred mixture of 3-cyclopentyloxy-4-methoxybenzaldehyde (54.9 grams, 249 mmol) and ammonium acetate (58.2 grams, 748 mmol) in ethanol (200 mL, 95%) was heated to 45° C. To the yellowish suspension, was added malonic acid (25.9 grams, 249 mmol) as a solid. The mixture was refluxed for 16 h. The mixture was cooled to room temperature. The suspension was filtered and the solid was washed with cold ethanol (200 mL) until the color was removed. The white solid was dried in a vacuum oven (45° C., 1 torr) to afford 3-amino-3-(3'-cyclopentoxy-4'-methoxyphenyl)propionic acid as white solid (41.97 grams, 61% yield): mp, 234.0°-235.0° C.; 1H NMR (CDCl3)δ1.62-1.98 (m, 8H, C5H8), 2.53 (d, J=7 Hz, 2H, CH2), 3.80 (s, 3H, CH3), 4.21 (t, J=7 Hz, 1H, OCH), 4.84-4.86 (m, 1H, NCH), 6.96-7.03 (m, 3H, Ar); 13C NMR (CDCl3)δ26.33, 34.97, 49.78, 55.32, 58.48, 83.99, 114.99, 116.04, 121.63, 140.63, 149.12, 150.75, 182.87; Anal Calcd for C15 H21NO4 : C, 64.50; H, 7.58; N, 5.01. Found: C, 64.54; H, 7.68; N, 4.93.
Workup
- temperatureThe mixture was refluxed for 16 h
- temperatureThe mixture was cooled to room temperature
- filtrationThe suspension was filtered
- washthe solid was washed with cold ethanol (200 mL) until the color
- customwas removed
- customThe white solid was dried in a vacuum oven (45° C., 1 torr)
Sources & evidence
- ORD record
- ord-455545fd7f014d1f870168a33106cb63
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05703098
Reaction notes
Loading…