Reacción #1289

ord-1a4951c4532f4cb2bdd53951628d0ded

Ecuación de reacción

[N-]=[N+]=NC1CCc2ccccc2NC1=O
3-azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one
C=CC(=O)OCC
ethyl acrylate
CC(C)(C)O
tert-butanol
[K]
potassium
→
CCOC(=O)CCN1C(=O)C(N=[N+]=[N-])CCc2ccccc21
3-azido-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-propanoic acid, ethyl ester

Reactantes

[N-]=[N+]=NC1CCc2ccccc2NC1=O
3-azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one
—
( a )
C=CC(=O)OCC
ethyl acrylate
CC(C)(C)O
tert-butanol
[K]
potassium

Reactivos

Ninguno

Disolventes

C1CCOC1.CC(C)(C)O
tetrahydrofuran tert-butanol
C1CCOC1
tetrahydrofuran

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

A solution of 3-azido-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one [prepared as described by Watthey et al., J. Med. Chem., 28, p. 1511-15156 (1985)] in tetrahydrofuran/tert-butanol was cooled to 0° C. and treated with ethyl acrylate and 1N tert-butanol, potassium salt/tetrahydrofuran according to the procedure of Example 40 part (a) affording 3-azido-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-propanoic acid, ethyl ester as a syrup. TLC (ethyl ether:hexane, 1:1) Rf =0.45.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723457uspto-grants-1998_03