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

HRID 1417389Notes

Reaction equation

HRID 1417389 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) δ 12.44 (br s, 1H, COOH), 7.36 (d, J=8.7 Hz, 2 H), 6.90 (d, 1 H, J=8.7 Hz), 5.64 (m, 1 H), 3.72 (s, 3 H), 3.35 (m, 2 H); 13C NMR (DMSO-d6) δ 171.5, 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-f89094c985cd4d219e4879940ae813ab
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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