3-Amino-3-(4-methoxyphenyl)propanoic acid → HCID 21250922, compound

HRID 1940077Notes

Reaction equation

HRID 1940077 reaction equation
[Cl:1][C:2]12[C:12]([Cl:13])=[C:11]([Cl:14])[C:10]([Cl:15])=[CH:9][CH:3]1[C:4]([O:6][C:7]2=[O:8])=O.[NH2:16][CH:17]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[CH2:18][C:19]([OH:21])=[O:20]>C(O)(=O)C>[Cl:1][C:2]12[C:12]([Cl:13])=[C:11]([Cl:14])[C:10]([Cl:15])=[CH:9][CH:3]1[C:4]([N:16]([CH:17]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[CH2:18][C:19]([OH:21])=[O:20])[C:7]2=[O:8])=[O:6]

Participants

4

Reactant 2

HCID 5858893-Amino-3-(4-methoxyphenyl)propanoic acidHCID 86750389HCID 86750389, compound

Product 1

HCID 21250922HCID 21250922, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 2,3,4,5-tetrachlorophthalic acid anhydride (2.85 g, 10.0 mmol) and 3-amino-3-(4-methoxyphenyl)propionic acid (1.95 g, 10.0 mmol) in 25 mL of acetic acid under nitrogen was heated to reflux for 4.5 hours. A solid formed as the reaction mixture cooled. The resulting slurry was filtered and the solid dried in vacuo (60° C., <2 mm) to afford 4.24 g (92%) of 3-(2,3,4,5-tetrachlorophthalimido)-3-(4-methoxyphenyl)-propionic acid as an off-white solid contaminated with~1% acetic acid: mp 235.6°-238° C.; 1H NMR (DMSO-d6) δ12.44 (br s, 1H, COOH), 7.36 (d, J=8.7 Hz, 2H), 6.90 (d, 1H, J=8.7 Hz), 5.64 (m, 1H), 3.72 (s, 3H), 3.35 (m, 2H); 13C NMR (DMSO-d6) δ171.5, 163.0, 158.8, 138.4, 129.9, 128.6, 128.2, 127.6, 113.8, 55.0, 50.2, 35.6. Anal. Calcd for C18H11NO5Cl4. Theory: C, 46.68; H, 2.39;N, 3.02. Found: C, 46.58; H, 2.31; N, 2.91.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 hours
  3. customA solid formed as the reaction mixture
  4. temperaturecooled
  5. filtrationThe resulting slurry was filtered
  6. customthe solid dried in vacuo (60° C., <2 mm)

Sources & evidence

ORD record
ord-a3329b3f2d464c3b901976e88d6909e4
Source dataset
uspto-grants-1997_12
Patent number
US05698579

Reaction notes

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