Sodium Carbonate → Methyl 3-phthalimido-3-(3-ethoxy-4-methoxyphenyl)propionate

HRID 1421321Notes

Reaction equation

HRID 1421321 reaction equation
Cl.[NH2:2][CH:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][CH3:19])[CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]2[C:32]1=[O:41])(OCC)=O>O.C(#N)C>[C:32]1(=[O:41])[N:2]([CH:3]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][CH3:19])[CH:10]=2)[CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 21250974Methyl 3-amino-3-(3-ethoxy-4-methoxyphenyl)propionate hydrochloride

Product 1

HCID 9821373Methyl 3-phthalimido-3-(3-ethoxy-4-methoxyphenyl)propionateYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of methyl 3-amino-3-(3-ethoxy-4-methoxyphenyl)propionate hydrochloride (0.87 g, 3.0 mmol) and sodium carbonate (0.32 g, 3.0 mmol) in a mixture of water (10 mL) and acetonitrile (10 mL) was added N-carbethoxyphthalimide (0.68 g, 3.0 mmol). The resulting solution was stirred for 3 hours at room temperature. The acetonitrile was removed in vacuo. To the resulting mixture was added ether (5 mL) and the mixture was stirred at room temperature overnight allowing the ether to evaporate. The resulting white solid was filtered. The solid was washed with water, air dried, and dried in vacuo (60° C.,<1 mm) to afford 1.0 g (87%) of methyl 3-phthalimido-3-(3-ethoxy-4-methoxyphenyl)propionate as a white solid: mp 86-87° C.; 1H NMR (CDCl3)δ 7.86-7.63 (m, 4H), 7.16-7.05 (m, 2H), 6.88-6.76 (m, 1H), 5.77 (dd, J=5.9, 10 Hz, 1H), 4.11 (q, J=7 Hz, 2H), 3.84 (s, 3H), 3.77 (dd, J=10, 6.7 Hz, 1H), 3.63 (s, 3H), 3.25 (dd, J=5.9, 16.5 Hz, 1H), 1.45 (t, J=7 Hz, 3H); 13C NMR (CDCl3)δ 171.0, 168.0, 149.0, 148.2, 133.9, 131.7, 130.9, 123.2, 120.2, 112.5, 111.1, 64.3, 55.8, 51.8, 50.7, 35.8, 14.6; HPLC (Waters Nova-Pak C18 column, 3.9×150 mm, 4 micron, 1 mL/min, 240 nm, 45/55, acetonitrile/0.1% aqueous phosphoric acid 6 min, 100%, Anal. Calcd. for C21H21NO6. Theoretical: C, 65.79; H, 5.52; N, 3.65. Found: C, 65.71; H, 5.70; N, 3.63.

Workup

  1. customThe acetonitrile was removed in vacuo
  2. additionTo the resulting mixture was added ether (5 mL)
  3. stirringthe mixture was stirred at room temperature overnight
  4. customto evaporate
  5. filtrationThe resulting white solid was filtered
  6. washThe solid was washed with water, air
  7. customdried
  8. customdried in vacuo (60° C.,<1 mm)

Sources & evidence

ORD record
ord-ce669dbcd4614265ad6efcf7d4cb9b7c
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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