Sodium Carbonate → HCID 9841465, compound

HRID 1531862Notes

Reaction equation

HRID 1531862 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:17])[CH2:6][CH:7]([NH2:16])[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:3].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39])(OCC)=O>O.C(#N)C>[C:30]1(=[O:39])[N:16]([CH:7]([C:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:17])[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 6603312HCID 6603312, compound

Product 1

HCID 9841465HCID 9841465, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-amino-3-(4-methoxyphenyl)propionic acid ethyl ester hydrochloride (1.00 g, 3.85 mmol) and sodium carbonate (0.41 g, 3.85 mmol) in 40 mL of water was added N-carboethoxyphthalimide (0.84 g, 3.85 mimol) in 10 mL of acetonitrile. The reaction was complete in one hour by TLC. The reaction mixture was partially concentrated to remove the acetonitrile. To the resulting mixture was added 0.5 mL of ethyl ether and the mixture was stirred for 1 hour at room temperature. The resulting slurry was filtered and the solid was washed with copious amounts of water. The solid was air-dried overnight to afford 1.02 g (75%) of ethyl 3-phthalimido-3-(4-methoxyphenyl)propionate as a white gum: mp 32° C.; 1H NMR (DMSO-d6, 250 MHz) δ7.86 (m, 4H), 6.90-7.37 (M, 4H), 5.66 (dd, 1H J1=7.5, J2=2.5), 4.00 (d, 2H, J=7.5) 3.3-3.6 (M, 2H), 1.04 (t, 3H, J=7.5 Hz); 13C (DMSO-d6) δ170.1, 167.5, 158.7, 134.7, 131.0, 130.5, 128.3, 123.2, 113.88, 60.1, 55.0, 49.5, 35.7, 13.8. Anal. Calcd for C20H19NO5: C, 67.98; H, 5.42; N, 3.90; Found C, 67.78; H. 5.30; N, 3.92.

Workup

  1. concentrationThe reaction mixture was partially concentrated
  2. customto remove the acetonitrile
  3. additionTo the resulting mixture was added 0.5 mL of ethyl ether
  4. filtrationThe resulting slurry was filtered
  5. washthe solid was washed with copious amounts of water
  6. customThe solid was air-dried overnight

Sources & evidence

ORD record
ord-ad9fb6af08b8480da613313f8967bbc5
Source dataset
uspto-grants-2001_03
Patent number
US06200987B1

Reaction notes

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