Potassium Hydroxide → 3-[N-(1-carboethoxy-3-phenylpropyl)amino]-5-carbomethoxymethyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

HRID 1632771Notes

Reaction equation

HRID 1632771 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[O:18][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[CH2:31][C:32]([O:34][CH3:35])=[O:33]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[C:1]([CH:6]([NH:15][CH:16]1[C:22](=[O:23])[N:21]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=2[O:18][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 204423383-[N-(1-carboethoxy-3-phenylpropyl)amino]-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

Product 1

HCID 204423513-[N-(1-carboethoxy-3-phenylpropyl)amino]-5-carbomethoxymethyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

An ice cold mixture of 81 mg of 3-[N-(1-carboethoxy-3-phenylpropyl)amino]-2,3-dihydro-1,5-benzoxazepin-4(5H)-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 is 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]-5-carbomethoxymethyl-2,3-dihydro-1,5-benzoxazepin-4(5H)-one; NMR (CDCl3) δ 6.35-8.00 (m, 10), 4.30-4.80 (m, 3), 3.67 (s, 3), 1.20 (t, 3); IR (neat) 3300 (NH), 1730 (C=O, ester), 1685 (C=O, lactam) cm-1.

Workup

  1. filtrationAt this time the solution is filtered
  2. concentrationconcentrated
  3. dissolutionthe residue is 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-9598c219b0064b45897a5b24d27ade9f
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

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