Reaktion #430226

ord-9f0a801a94474906bc428c5344d6cdab

Reaktionsgleichung

[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

Edukte

[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

Reagenzien

Keine

Lösungsmittel

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

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05859239uspto-grants-1999_01