Methyl 2-[(4-ethoxy-4-oxobutyl)(4-methylbenzene-1-sulfonyl)amino]benzoate → Ethyl 5-oxo-1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylate

HRID 2353858

Reaction equation

HRID 2353858 reaction equation
CC(C)([O-])C.[K+].CO[C:9](=[O:35])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N:16]([CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C1(C)C=CC=CC=1>[CH2:33]([O:32][C:30]([CH:29]1[CH2:28][CH2:27][N:16]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]1=[O:35])=[O:31])[CH3:34]

Participants

4

Reactant 2

HCID 266879Methyl 2-[(4-ethoxy-4-oxobutyl)(4-methylbenzene-1-sulfonyl)amino]benzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 12435934Ethyl 5-oxo-1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylateYield 64.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a heated mixture of potassium t-butoxide (371 g, 3.58 mol) in toluene (4 l) at 70° C. was added 2-[(3-Ethoxycarbonyl-propyl)-(toluene-4-sulfonyl)-amino]-benzoic acid methyl ester (750 g, 1.79 mol). After the addition was completed, the mixture was cooled to room temperature then poured into ice water. The extraction with CH2Cl2 was successively done, and organic layer was dried over MgSO4 and concentrated under reduced pressure to afford crude compound 5-Oxo-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester (450 g) as a mixture of Me and Et esters.

Workup

  1. additionAfter the addition
  2. extractionThe extraction with CH2Cl2
  3. dry with materialorganic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb399ab49b87459cba822030f4626328
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Linked notes

Loading…