Sodium Acetate → HCID 58241345, compound

HRID 2257966Notes

Reaction equation

HRID 2257966 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:19]([O-:22])(=O)[CH3:20].[Na+]>C(O)(=O)C>[C:5]1(=[O:6])[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:19](=[O:22])[C@H:20]2[CH2:11][CH2:10][CH2:9][CH2:3][C@@H:4]12

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 16277031Methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride

Product 1

HCID 58241345HCID 58241345, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 1,2,5,6-hexahydrophthalic anhydride (0.77 grams, 5.0 mmol), methyl 3-amino-3-(3,4-dimethoxyphenyl)propionate hydrochloride (1.38 grams, 5.0 mmol), and sodium acetate (0.40 grams, 4.9 mmol) in 20 mL of acetic acid under N2 was heated to reflux for 20 hours. The cooled reaction mixture was concentrated in vacuo and the residue diluted with 25 mL of methylene chloride and then 25 mL of sat. sodium bicarbonate was added in portions and the resulting mixture stirred for 30 minutes. The organic phase was separated, dried (sodium sulfate), and concentrated to afford the crude product as an oil. The crude product was purified by flash chromatography (silica gel, 1/9 EtOAc/hexanes) to afford 0.72 grams (38%) of methyl 3-(cis-hexahydrophthalimido)-3-(3,4-dimethoxyphenyl)propionate as an off-white solid (wax): mp 92.5°-95° C.; 1H NMR (CDCl3 /TMS) δ 7.02 (m, 2H, Ar), 6.65 (m, 1H, Ar), 5.56 (dd, J=5.5, 10.5 Hz, 1H CHN), 3.86 (2 s, 6H, 2 OCH3), 3.74 (dd, J=16.5, 10.5 Hz, 1H), 3.66 (s, 3H, OCH3), 3.08 (dd, J=5.5, 16.5 Hz, 1H, CHCO), 2.77 (m, 2H, bridgehead Hs), 1.87-1.55 (m, 4H), 1.5-1.2 (m, 4H); 13C NMR (CDCl3 /TMS) δ 179.5, 179.4, 171.1, 148.9, 148.8, 130.9, 120.1, 111.0, 110.9, 55.9, 55.8, 51.8, 51.0, 39.6, 35.2, 23.6, 23.5, 21.6; TLC (1/9 EtOAc/hexanes, UV) Rf =0.36. Anal. Calcd for C20H25NO6. Theory C, 63.99; H, 6.71; N, 3.73. Found C, 63.89; H, 6.81; N, 3.61.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated in vacuo
  5. additionthe residue diluted with 25 mL of methylene chloride
  6. addition25 mL of sat. sodium bicarbonate was added in portions
  7. customThe organic phase was separated
  8. dry with materialdried (sodium sulfate)
  9. concentrationconcentrated
  10. customto afford the crude product as an oil
  11. customThe crude product was purified by flash chromatography (silica gel, 1/9 EtOAc/hexanes)

Sources & evidence

ORD record
ord-6a64abc6e29d41cdab6375b5dbbcb4a0
Source dataset
uspto-grants-1997_08
Patent number
US05658940

Reaction notes

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