Hydrochloric Acid → alpha-Methyl-[2-(2-amino-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

HRID 580391Notes

Reaction equation

HRID 580391 reaction equation
[CH3:1][C:2]([CH:11]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[N+:23]([O-])=O)([C:7]([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4].Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][C:2]([CH:11]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:16]=[CH:15][C:14]=1[NH2:23])([C:7]([O:9][CH3:10])=[O:8])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate2×HCID 15128660alpha-Methyl-[2-(2-nitro-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

Product 1

HCID 15128675alpha-Methyl-[2-(2-amino-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl esterYield 91.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

α-Methyl-[2-(2-nitro-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (6.80 g; 14.9 mmole) was dissolved in methanol (200 ml) under argon at room temperature. Powdered stannous chloride dihydrate (17.48 g; 77.5 mmole) was added, followed by concentrated hydrochloric acid (19 ml) with stirring. After 1.5 hours, Celite, ethyl acetate and saturated potassium carbonate solution were added with stirring (the potassium carbonate was added portionwise). The suspension was filtered through a Celite pad. The pad was then rinsed with ethyl acetate (three times). The filtrate was concentrated and the resulting white solid was triturated with 10% methanol:water and dried giving 6.02 g of the title compound.

Workup

  1. additionwas added portionwise)
  2. filtrationThe suspension was filtered through a Celite pad
  3. washThe pad was then rinsed with ethyl acetate (three times)
  4. concentrationThe filtrate was concentrated
  5. customthe resulting white solid was triturated with 10% methanol
  6. dry with materialwater and dried

Sources & evidence

ORD record
ord-d5997e074f17407ba551d413daa374f5
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

Loading…