Diethyl Ether → Methyl 3-phthalimido-3-(3,4-dimethoxyphenyl)propionate

HRID 1417398Notes

Reaction equation

HRID 1417398 reaction equation
Cl.[NH2:2][CH:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])(OCC)=O.CCOCC>C(#N)C.O>[C:31]1(=[O:40])[N:2]([CH:3]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=2)[CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]12

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 16277031Methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride

Product 1

HCID 461664Methyl 3-phthalimido-3-(3,4-dimethoxyphenyl)propionateYield 92%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A mixture of methyl 3-amino-3-(3,4-dimethoxyphenyl)propionate hydrochloride (1.38 g, 5.00 mmol), sodium carbonate (0.53 g, 5.00 mmol), and N-carbethoxyphthalimide (1.10 g, 5.0 mmol) in 40 mL of acetonitrile/water (1/1) was stirred for 1 hour at room temperature. The reaction solution was then partially concentrated under reduced pressure to remove the acetonitrile. This afforded a white gum in water. To the mixture was then added 5 mL of ether and the mixture was stirred for 2 hours. The resulting slurry was filtered, the solid was washed with a copious amount of water and air-dried overnight to afford 1.69 g (92%) of methyl 3-phthalimido-3-(3,4-dimethoxyphenyl)propionate as a white solid: mp 114.1°-115.6° C.; 1H NMR (DMSO-d6, 250 MHz)d 7.80-7.95 (m, 4 H, Ar), 6.80-7.10 (m, 3 H, Ar), 5.65 (dd, 1 H, J1 =7 Hz, J2 =9 Hz), 3.74 (s, 3 H, OCH3), 3.72 (s, 3 H, OCH3), 3.55 (s, 3 H, OCH3), 3.30-3.67 (m, 2 H); 13C NMR d(DMSO-d6)d 170.8, 167.6, 148.6, 148.4, 134.7, 131.1, 131.0, 123.2, 119.3, 111.7, 111.0, 55.5, 51.6, 49.9, 35.6. Anal. Calcd for C20H19NO6. Theoretical C, 65.03; H, 5.18; N, 3.79. Found C, 65.17; H, 5.14; N, 3.75. HPLC 99%.

Workup

  1. concentrationThe reaction solution was then partially concentrated under reduced pressure
  2. customto remove the acetonitrile
  3. customThis afforded a white gum in water
  4. stirringthe mixture was stirred for 2 hours
  5. filtrationThe resulting slurry was filtered
  6. washthe solid was washed with a copious amount of water
  7. customair-dried overnight

Sources & evidence

ORD record
ord-b7a96830ca38479ab454be5dad8e34d4
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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