Reaction #7140

ord-0d22981a7dc349ca9113c23a40cea26a

Reaction equation

NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1
cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide
COC(=O)c1ccc(CBr)cc1
methyl 4-(bromomethyl)benzoate
→
COC(=O)c1ccc(CN([C@@H]2CCCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1
titled compound
Yield 28.0%
COC(=O)c1ccc(CN([C@@H]2CCCCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1
cis-4-[[(2-Carbamoyl-cycloheptyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-benzoic acid methyl ester
Yield 28.0%

Reactants

NC(=O)[C@@H]1CCCCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1
cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide
COC(=O)c1ccc(CBr)cc1
methyl 4-(bromomethyl)benzoate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The titled compound (321 mg) was prepared in 28% yield from cis-2-(4-chlorobenzenesulfonylamino)-cycloheptanecarboxylic acid amide (800 mg, 2.42 mmol) and methyl 4-(bromomethyl)benzoate according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.83 (m, 4 H), 7.65 (d, 2 H,J=8.0 Hz), 7.45 (d, 2 H, J=12.0 Hz), 7.31 (s br, 1 H), 6.64 (s br, 1 H), 4.60 (AB2,2 H,Δv=16,Jab=92 Hz), 3.96 (m, 1 H), 3.85 (m, 3 H), 2.78 (m, 1 H), 2.28 (m, 1 H), 1.72 (m, 2 H), 1.35 (m, 7 H); MS m/e 479.12 (M+H)+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07084178B2uspto-grants-2006_08