Sodium Carbonate → HCID 9822889, compound

HRID 1940091Notes

Reaction equation

HRID 1940091 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][CH2:19][CH2:20][CH3:21])[CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43])(OCC)=O>O.C(#N)C>[C:34]1(=[O:43])[N:2]([CH:3]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:10]=2)[CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 21250957HCID 21250957, compound

Product 1

HCID 9822889HCID 9822889, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of methyl 3-amino-3-(3-butoxy-4-methoxyphenyl)propionate hydrochloride (0.95 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 1.1 g (89%) of methyl 3-phthalimido-3-(3-butoxy-4-methoxyphenyl)propionate as a white solid: mp 54°-55° C.; 1H NMR (CDCl3) δ5 7.86-7.63 (m, 4H), 7.16-7.05 (m, 2H), 6.85-6.76 (m, 1H), 5.76 (dd, J=5.9, 10 Hz, 1H), 4.02 (t, J=6.7 Hz, 3.86-3.71 (m, 1H), 3.83 (s, 3H), 3.63 (s, 3H), 3.24 (dd, J=5.9, 16.5 Hz, 1H), 1.89-1.73 (m, 2H), 1.59-1.41 (m, 2H), 1.04-0.89 (m, 3H); 13C NMR (CDCl3) δ5 171.1, 168.1, 149.2, 148.5, 133.9, 131.8, 130.9, 123.3, 120.2, 112.7, 111.4, 68.6, 55.9, 51.9, 50.7, 35.9, 31.1, 19.2, 13.9; HPLC (Waters Nova-Pak C18 column, 3.9×150 mm, 4 micron, 1 mL/min, 240 nm, 55/45, acetonitrile/0.1% aqueous phosphoric acid) 6.5 min, 100%, Anal. Calcd. for C23H2 NO6. Theoretical: C, 67.14; H, 6.12; N, 3.40. Found: C, 66.89; H, 6.15; N, 3.31.

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-fa8dae85676d4359a85f9424fdabf422
Source dataset
uspto-grants-1997_12
Patent number
US05698579

Reaction notes

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