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

HRID 580403Notes

Reaction equation

HRID 580403 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[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[NH2:25])([C:9](OC)=[O:10])[C:5]([O:7][CH3:8])=[O:6])[CH:2]=[CH2:3].C[O-].[Na+].CN(C)[CH:39]=[O:40].Cl>CO>[CH3:8][O:7][C:5]([C:4]1([CH2:1][CH:2]=[CH2:3])[CH:13]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=2[O:40][CH3:39])[CH2:14][C:15]2[CH:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:18]=[CH:17][C:16]=2[NH:25][C:9]1=[O:10])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 15128676(2-Propenyl)-[2-(2-amino-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester

Product 1

HCID 201351131,3,4,5-Tetrahydro-3-(methoxycarbonyl)-4-(methoxyphenyl)-3-(2-propenyl)-7-(trifluoromethyl)-2H-1-benzazepin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

α-(2-Propenyl)-[2-(2-amino-5-trifluoromethylphenyl)-1-(4-methoxyphenyl)ethyl]propanedioic acid, dimethyl ester (47.47 g; 0.102 mole) and a 25% (by weight) solution of sodium methoxide in methanol (107 ml; 0.469 mole; d=0.945; 4.6 eq.) in methanol (200 ml) and dry dimethylformamide (200 ml) was refluxed (~95° C.) overnight. 1N Hydrochloric acid was added with stirring, producing a precipitate that was collected by suction-filtration and triturated with water (two times). The solid was slurried in carbon tetrachloride and rotary evaporated followed by vacuum drying to give 42.99 g of crude product.

Workup

  1. customproducing a precipitate that
  2. filtrationwas collected by suction-filtration
  3. customtriturated with water (two times)
  4. customrotary evaporated
  5. customdrying

Sources & evidence

ORD record
ord-573310422b0e4010a72e023381ff9324
Source dataset
uspto-grants-1988_06
Patent number
US04752645

Reaction notes

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