Reaction #1904070

ord-fa2608c6ac90411ab9346e15f2cb6fb1

Reaction equation

CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C(C)(c1ccccc1)OCC(=O)N2
tert-butyl-2-(5-methyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate
O=C=NS(=O)(=O)Cl
chlorosulfonyl isocyanate
→
CC(C)(C)OC(=O)n1c(C#N)ccc1-c1ccc2c(c1)C(C)(c1ccccc1)OCC(=O)N2
tert-Butyl-2-cyano-5-(5-methyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate

Reactants

CC(C)(C)OC(=O)n1cccc1-c1ccc2c(c1)C(C)(c1ccccc1)OCC(=O)N2
tert-butyl-2-(5-methyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate
O=C=NS(=O)(=O)Cl
chlorosulfonyl isocyanate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

tert-Butyl-2-cyano-5-(5-methyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate was prepared from tert-butyl-2-(5-methyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepin-7-yl)-1H-pyrrole-1-carboxylate and chlorosulfonyl isocyanate according to the cyanation procedure described in example 1. 1H-NMR (DMSO-d6) δ 10.02 (s, 1H), 7.42-7.38 (m, 2H), 7.32-7.10 (m, 7H), 6.49 (d, J=3.80 Hz, 1H), 4.20 (d, J=14.63 Hz, 1H), 3.99, (d, J=14.41 Hz, 1H), 1.87 (s, 3H), 1.39 (s, 9H); MS (ES) m/z 442 ([M−H]−, 100%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07598237B2uspto-grants-2009_10