Hydrochloric Acid → HCID 20135070, compound

HRID 580407Notes

Reaction equation

HRID 580407 reaction equation
[CH2:1]([C:4]([CH:13]([C:26]1[CH:31]=[CH:30][C:29](OC)=[CH:28][CH:27]=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[NH2:25])([C:9]([O:11][CH3:12])=[O:10])[C:5]([O:7]C)=O)[CH:2]=[CH2:3].C[O-].[Na+].CN(C)[CH:39]=[O:40].Cl>CO>[CH3:12][O:11][C:9]([C:4]1([CH2:1][CH:2]=[CH2:3])[CH:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:40][CH3:39])[CH2:14][C:15]2[C:20]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:18]=[CH:17][C:16]=2[NH:25][C:5]1=[O:7])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 15128673alpha-(2-Propenyl)-[2-(2-amino-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

Product 1

HCID 20135070HCID 20135070, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

α-(2-Propenyl)-[2-(2-amino-6-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (9.03 g; 19.4 mmole) and a 25% (by weight) sodium methoxide in methanol solution (20.5 ml; 89.5 mmole; d=0.945; 4.6 eq.) in methanol (100 ml) and dry dimethylformamide (100 ml) were refluxed (~95° C. for four hours. 1N Hydrochloric acid was added with stirring, producing a precipitate that was collected by suction-filtration, washed with water (three times) and dried in vacuo giving ~10 g of the title compound as a solid. The "crude" material was used "as is".

Workup

  1. customproducing a precipitate that
  2. filtrationwas collected by suction-filtration
  3. washwashed with water (three times)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-80fbf5cdb00a4a1c85d207ae411bf727
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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