Hydrochloric Acid → 1,3,4,5-Tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-3-methyl-7-(trifluoromethyl)-2H-1-benzazepin-2-one

HRID 580392Notes

Reaction equation

HRID 580392 reaction equation
C[O-].[Na+].[CH3:4][C:5]([CH:14]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[NH2:26])([C:10]([O:12]C)=O)[C:6]([O:8][CH3:9])=[O:7].CN(C)C=O.Cl>CO>[CH3:9][O:8][C:6]([C:5]1([CH3:4])[CH:14]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:19]=[CH:18][C:17]=2[NH:26][C:10]1=[O:12])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 15128675alpha-Methyl-[2-(2-amino-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

Product 1

HCID 151286881,3,4,5-Tetrahydro-3-(methoxycarbonyl)-4-(4-methoxyphenyl)-3-methyl-7-(trifluoromethyl)-2H-1-benzazepin-2-oneYield 88.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 25% (by weight) sodium methoxide in methanol solution (14.2 ml; 625 mmole; 4.6 eq.; d=0.945) and α-methyl-[2-(2-amino-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (5.96 g; 13.56 mmole) in methanol (30 ml) and dry dimethylformamide (35 ml) were refluxed (~95° C.) overnight. 1N Hydrochloric acid was added with stirring producing a white precipitate that was collected by suction-filtration, washed with water (three times) and dried in vacuo giving 4.88 g of a white solid which contained an impurity as shown by NMR. The impurity disappeared after the sample stood overnight.

Workup

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

Sources & evidence

ORD record
ord-397e023bc0a64daeb82a1f4feedaeeda
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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