Sodium Methoxide → 1-ethoxycarbonylmethyl-3-(1-ethoxycarbonyl-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepine-2-one

HRID 2418758Notes

Reaction equation

HRID 2418758 reaction equation
[CH2:1]([O:3][C:4]([CH:6]([NH:15][CH:16]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:17](OCC)=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].C[O-].[Na+]>CO>[CH2:35]([O:34][C:32]([CH2:31][N:30]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][CH2:22][CH:16]([NH:15][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:17]1=[O:18])=[O:33])[CH3:36]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 53634656Ethyl 2-(1-ethoxycarbonyl-3-phenylpropylamino)-4-[o-(ethoxycarbonylmethylamino)phenyl]butyrate

Product 1

HCID 132435171-ethoxycarbonylmethyl-3-(1-ethoxycarbonyl-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepine-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of ethyl 2-(1-ethoxycarbonyl-3-phenylpropylamino)-4-[o-(ethoxycarbonylmethylamino)phenyl]butyrate (5.6 g) in methanol (100 ml) is added to a solution of sodium methoxide in methanol [prepared from sodium (0.25 g) and methanol (50 ml)] with stirring under a nitrogen atmosphere. The reaction mixture is refluxed for 65 hours, then evaporated under reduced pressure. The residue is distributed between water (50 ml) and dichloromethane (200 ml). The aqueous solution is extracted with dichloromethane (200 ml) and the combined organic solutions washed with water (50 ml) and dried over potassium carbonate. Evaporation of the solvent gives as a mixture of isomers A and B of 1-ethoxycarbonylmethyl-3-(1-ethoxycarbonyl-3-phenylpropylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, which is separated by chromatography on silica gel and converted to the individual maleate salts as described in example 10.

Workup

  1. temperatureThe reaction mixture is refluxed for 65 hours
  2. customevaporated under reduced pressure
  3. extractionThe aqueous solution is extracted with dichloromethane (200 ml)
  4. washthe combined organic solutions washed with water (50 ml)
  5. dry with materialdried over potassium carbonate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e744c1cc9f5b4bc9ac5de6c1632b0e93
Source dataset
uspto-grants-1984_09
Patent number
US04473575

Reaction notes

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