3,4,5,6-Tetrahydrophthalic anhydride → HCID 22924027, compound

HRID 2257967Notes

Reaction equation

HRID 2257967 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.Cl.[NH2:13][CH:14]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)[CH2:15][C:16]([O:18][CH3:19])=[O:17].C([O-])(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[C:4]1(=[O:6])[N:13]([CH:14]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:1](=[O:11])[C:2]2[CH2:10][CH2:9][CH2:8][CH2:7][C:3]1=2

Participants

7

Reactant 4

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 16277031Methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride

Product 1

HCID 22924027HCID 22924027, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 3,4,5,6-tetrahydrophthalic anhydride (0.38 grams, 2.5 mmol) and methyl 3-amino-3-(3,4-dimethoxyphenyl)propionate hydrochloride (0.69 grams, 2.5 mmol) in acetic acid (10 mL) was added sodium acetate (0.21 grams, 2.5 mmol). The suspension was refluxed under nitrogen overnight. The acetic acid was removed in vacuo to afford an orange oil which was taken up in water (5 mL) and the pH was adjusted to 7 using a saturated solution of sodium bicarbonate. The resulting mixture was extracted with methylene chloride (3×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 0.62 grams of crude product as a yellow oil. The crude product was purified by flash chromatography (silica gel, 35% ethyl acetate/hexane) and the resulting solid was dried in vacuo (60° C., <1 mm) to afford 0.22 g (23%) of product as a pale yellow solid: 1H NMR (CDCl3) δ 7.09-6.99(m, 2H), 6.84-6.75(m, 1H), 5.60-5.48(m, 1H), 3.87(s, 3H), 3.85(s, 3H), 3.71-3.55(m, 1H), 3.65(s, 3H), 3.23-3.06(m, 1H), 2.38-2.21(m,4H), 1.85-1.64(m, 4H); 13C NMR (CDCl3) δ 171.1, 170.8, 148.9, 148.7, 120.1, 111.2, 110.9, 55.9, 55.8, 50.4, 36.1, 21.2, 19.9. Anal. Calcd for C20H23NO6. Theoretical: C, 64.33; H, 6.21; N, 3.75. Found: C, 64.25; H, 6.10; N, 3.70.

Workup

  1. temperatureThe suspension was refluxed under nitrogen overnight
  2. customThe acetic acid was removed in vacuo
  3. customto afford an orange oil which
  4. extractionThe resulting mixture was extracted with methylene chloride (3×20 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford 0.62 grams of crude product as a yellow oil
  9. customThe crude product was purified by flash chromatography (silica gel, 35% ethyl acetate/hexane)
  10. customthe resulting solid was dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-dadb06752d5a49bd936aed33a8c592ee
Source dataset
uspto-grants-1997_08
Patent number
US05658940

Reaction notes

Loading…