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

HRID 1531874Notes

Reaction equation

HRID 1531874 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, 1 H, 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-cb0831441c4f4b8da8b0ea4e1b6cc013
Source dataset
uspto-grants-2001_03
Patent number
US06200987B1

Reaction notes

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