Hydrochloric Acid → alpha-(2-Propenyl)-[2-(2-amino-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

HRID 580406노트

반응식

HRID 580406 반응식
[CH2:1]([C:4]([CH:13]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[CH2:14][C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][C:16]=1[N+:25]([O-])=O)([C:9]([O:11][CH3:12])=[O:10])[C:5]([O:7][CH3:8])=[O:6])[CH:2]=[CH2:3].Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([C:4]([CH:13]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[CH2:14][C:15]1[C:20]([C:21]([F:22])([F:24])[F:23])=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:25])([C:9]([O:11][CH3:12])=[O:10])[C:5]([O:7][CH3:8])=[O:6])[CH:2]=[CH2:3]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate2회HCID 15128658alpha-(2-Propenyl)-[2-(2-nitro-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

생성물 1

HCID 15128673alpha-(2-Propenyl)-[2-(2-amino-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester수율 110.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

α-(2-Propenyl)-[2-(2-nitro-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (15.42 g; 31.12 mmole) was dissolved in methanol (110 ml) under argon at room temperature. Powdered stannous chloride dihydrate (36.52 g; 161.8 mmol; 5.2 eq.) was added followed by concentrated hydrochloric acid (50 ml) with stirring. After ~1.5 hours, Celite, ethyl acetate, and saturated potassium carbonate solution were added with stirring (the potassium carbonate solution was added portionwise). The suspension was filtered, and the solid rinsed with ethyl acetate (three times). The filtrate was concentrated, and the residue was washed with 10% methanol/water. The washings were concentrated and dried in vacuo giving ~16 g of a yellow oil. The solids (tin salts, Celite, potassium bicarbonate, etc.) that had been filtered from the reaction mixture were triturated in acetone (several times) and suction filtered through a pad of Celite. The acetone filtrate was concentrated, and the remaining residue was partitioned between chloroform and water. The chloroform layer was dried (magnesium sulfate) and concentrated, leaving 9.06 g of the title compound as a solid. The remaining product was assumed to be in the aforementioned ~16 g of yellow oil. The yellow oil was used "as is" in the next step, as was the 9.06 g of solid.

후처리

  1. waitAfter ~1.5 hours
  2. additionwas added portionwise)
  3. filtrationThe suspension was filtered
  4. washthe solid rinsed with ethyl acetate (three times)
  5. concentrationThe filtrate was concentrated
  6. washthe residue was washed with 10% methanol/water
  7. concentrationThe washings were concentrated
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-85e6fe36cfc040669d6288aa8c9f4fee
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04752645

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