Diethyl Ether → 3-Phthalimido-3-(4-benzyloxy-3-methoxyphenyl)propionic acid

HRID 1940078Notes

Reaction equation

HRID 1940078 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:9]([O:21][CH3:22])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]2[C:35]1=[O:44])(OCC)=O.CCOCC>O.C(#N)C>[C:35]1(=[O:44])[N:1]([CH:2]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:9]([O:21][CH3:22])[CH:8]=2)[CH2:3][C:4]([OH:6])=[O:5])[C:38](=[O:39])[C:37]2=[CH:40][CH:41]=[CH:42][CH:43]=[C:36]12

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 52302833-Amino-3-[4-(benzyloxy)-3-methoxyphenyl]propanoic acid

Product 1

HCID 98028103-Phthalimido-3-(4-benzyloxy-3-methoxyphenyl)propionic acidYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-amino-3-(4-benzyloxy-3-methoxyphenyl)propionic acid (1.505 g, 5.00 mmol) and sodium carbonate (0.572 g, 5.40 mmol) in a mixture of 75 mL of water and 175 mL of acetonitrile (mixture was warmed gently to dissolve solid) was added N-carbethoxyphthalimide (1.096 g, 5.00 mmol). The mixture was stirred for 1 hour, then partially concentrated in vacuo to remove the acetonitrile. A small amount of solid formed which was removed by filtration. The pH of the solution was adjusted to 1 with 4N Hydrochloric acid, a gum formed. To the stirred mixture was added 1 mL of ether and the mixture was then stirred overnight. The resulting slurry was filtered and the solid dried to afford 1.63 g (75%) of 3-phthalimido-3-(4-benzyloxy-3-methoxyphenyl)-propionic acid as a white powder, 1H NMR (DMSO-d6) δ12.43 (br s, 1H, COOH), 8.0-7.8 (m, 4H, Ar), 7.60-7.25 (m, 5H), 7.15-6.85 (m, 3H, Ar), 5.25 (dd, 1H, J=9, 6.6 Hz), 5.05 (s, 2H, OCH2), 3.76 (s, 3H, OMe), 3.52 (dd, 1H, J=9, 16.5 Hz), 2.29 (dd, 1 H, J=6.6, 16.5 Hz); 13C NMR (DMSO-d6) δ171.7, 167.6, 148.9, 147.3, 137.0, 134.6, 131.7, 131.0, 128.3, 127.7, 127.6, 123.1, 119.1, 113.3, 111.3, 69.8, 55.5, 50.1, 36.0. Anal. Calcd for C25H21N1O6. Theory: C, 69.66; H, 4.91; N, 3.25. Found: C, 69.50; H, 4.85; N, 3.22.

Workup

  1. temperaturewas warmed gently
  2. dissolutionto dissolve solid)
  3. concentrationpartially concentrated in vacuo
  4. customto remove the acetonitrile
  5. customA small amount of solid formed which
  6. customwas removed by filtration
  7. customa gum formed
  8. stirringthe mixture was then stirred overnight
  9. filtrationThe resulting slurry was filtered
  10. customthe solid dried

Sources & evidence

ORD record
ord-3a38c209b50f47e3807c6211e51e342d
Source dataset
uspto-grants-1997_12
Patent number
US05698579

Reaction notes

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