Reaction #1891

ord-757632750487427b80394903b6f82440

Reaction equation

CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(C#N)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21
trans-7-chloro-5-(2-chlorophenyl)-3-(3-cyanophenylaminocarbonylmethyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water
→
CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(-c3nnn[nH]3)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21
crystal
Yield 50.9%
CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(-c3nnn[nH]3)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21
Trans-7-chloro-5-(2-chlorophenyl)-1-neopentyl-3-[3-(tetrazol-5-yl)phenylaminocarbonylmethyl]-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine
Yield 50.9%

Reactants

CC(C)(C)CN1C(=O)[C@@H](CC(=O)Nc2cccc(C#N)c2)O[C@H](c2ccccc2Cl)c2cc(Cl)ccc21
trans-7-chloro-5-(2-chlorophenyl)-3-(3-cyanophenylaminocarbonylmethyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water

Reagents

None

Solvents

CN(C)C=O
dimethylformamide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Washthe mixture was washed with water
  2. 2
    Otherafter which the solvent was removed

Procedure

A solution of 0.2 g of trans-7-chloro-5-(2-chlorophenyl)-3-(3-cyanophenylaminocarbonylmethyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine and 80 mg of sodium azide in 5 ml of dimethylformamide was stirred at 90° C. for 60 hours. After water was added, the mixture was washed with water, after which the solvent was removed and the residue was subjected to silica gel column chromatography to yield 0.11 g of a crystal.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726306uspto-grants-1998_03