Potassium Hydroxide → 3-[N-(1-carboethoxy-3-phenylpropyl)amino]-1-carbomethoxymethyl-5-methyl-1,3,4,5-tetrahydro-1,5-benzo diazepin-2-one

HRID 1632775Notes

Reaction equation

HRID 1632775 reaction equation
[C:1]([CH:6]([NH:15][CH:16]1[C:22](=[O:23])[NH:21][C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[N:18]([CH3:28])[CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O:3][CH2:4][CH3:5])=[O:2].[OH-].[K+].Br[CH2:32][C:33]([O:35][CH3:36])=[O:34]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[C:1]([CH:6]([NH:15][CH:16]1[C:22](=[O:23])[N:21]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[N:18]([CH3:28])[CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 60984Methyl bromoacetateHCID 204423303-[N-(1-carboethoxy-3-phenylpropyl)amino]-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

Product 1

HCID 204423463-[N-(1-carboethoxy-3-phenylpropyl)amino]-1-carbomethoxymethyl-5-methyl-1,3,4,5-tetrahydro-1,5-benzo diazepin-2-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

An ice cold mixture of 84 mg of 3-[N-(1-carboethoxy-3-phenylpropyl)amino]-5-methyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2-one, 15 mg of powdered potassium hydroxide and 6.5 mg of tetrabutylammonium bromide in 3 ml of dry tetrahydrofuran is treated with 32 mg of methyl bromoacetate. The reaction is allowed to stir for 3 hr at room temperature. At this time, the solution is filtered and concentrated and the residue dissolved in 20 ml of ethyl acetate. This is washed with 5 ml of water and dried over potassium carbonate. Concentration under reduced pressure affords 3-[N-(1-carboethoxy-3-phenylpropyl)amino]-1-carbomethoxymethyl-5-methyl-1,3,4,5-tetrahydro-1,5-benzo diazepin-2-one.

Workup

  1. filtrationAt this time, the solution is filtered
  2. concentrationconcentrated
  3. dissolutionthe residue dissolved in 20 ml of ethyl acetate
  4. washThis is washed with 5 ml of water
  5. dry with materialdried over potassium carbonate
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-1079f0bfada64d4284a9b89e31e37eb6
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

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