Reaction #7147

ord-8e371e35fc1e435e8257067758daaf41

Reaction equation

NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1
cis-2-(4-chlorobenzenesulfonylamino)-cyclopentanecarboxylic acid amide
COC(=O)c1ccc(CBr)cc1
methyl 4-(bromomethyl)benzoate
→
COC(=O)c1ccc(CN([C@@H]2CCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1
titled compound
Yield 43.0%
COC(=O)c1ccc(CN([C@@H]2CCC[C@@H]2C(N)=O)S(=O)(=O)c2ccc(Cl)cc2)cc1
cis-4-[[(2-Carbamoyl-cyclopentyl)-(4-chlorobenzenesulfonyl)-amino]-methyl]-benzoic acid methyl ester
Yield 43.0%

Reactants

NC(=O)[C@@H]1CCC[C@@H]1NS(=O)(=O)c1ccc(Cl)cc1
cis-2-(4-chlorobenzenesulfonylamino)-cyclopentanecarboxylic 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 (161 mg) was prepared in 43% yield from cis-2-(4-chlorobenzenesulfonylamino)-cyclopentanecarboxylic acid amide (250 mg, 0.83 mmol) and methyl 4-(bromomethyl)benzoate according to the N-alkylation procedure described in Example 11: 1H NMR (DMSO-d6) δ 7.82 (d, 2 H, J=8.0 Hz), 7.75 (d, 2 H, J=8.0 Hz), 7.58 (d, 2 H, J=8.0 Hz), 7.33 (d, 2 H, J=8.0 Hz), 7.02 (s br, 1 H), 6.75 (s br, 1 H), 4.67 (AB2,2 H,Δv=20,Jab=24 Hz), 4.33 (m, 1 H), 3.84 (s, 3 H), 2.84 (m, 1 H), 1.73 (m, 4 H), 1.48 (m, 2 H); MS m/e 451.01 (M+H)+.

Source

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