trans-1-Benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-methanol → trans-1-Benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-carboxylic acid

HRID 1784

Reaction equation

HRID 1784 reaction equation
[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[C@@H:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[O:11][C@H:10]([CH2:27][OH:28])[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:32].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[C@@H:12]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[O:11][C@H:10]([C:27]([OH:32])=[O:28])[C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69945577trans-1-Benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-methanolHCID 131709961Jones' reagent

Product 1

HCID 69946653trans-1-Benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 20 ml of acetone was dissolved 0.5 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-methanol obtained in Example 46. To the solution was added dropwise, while stirring at room temperature, 0.5 ml of a Jones reagent. The reaction mixture was stirred for one hour at room temperature, which was then concentrated under reduced pressure The concentrate was subjected to extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off under reduced pressure. From the residue was obtained 0.23 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-carboxylic acid as white crystals, m.p.177°-178 C.

Workup

  1. additionTo the solution was added dropwise
  2. stirringThe reaction mixture was stirred for one hour at room temperature
  3. concentrationwhich was then concentrated under reduced pressure The concentrate
  4. extractionwas subjected to extraction with ethyl acetate
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-42aca8051c1945bf90df0b26f4fe3c47
Source dataset
uspto-grants-1998_03
Patent number
US05726306

Linked notes

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