Ethyl Acetate → HCID 59497772, compound

HRID 1011506Notes

Reaction equation

HRID 1011506 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:17][OH:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=1.C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][CH:28]=2)[C@@H:12]2[CH2:16][CH2:15][CH2:14][C@H:13]2[CH2:17][OH:18])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 869964-(Bromomethyl)benzonitrileHCID 594977994-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamide

Product 1

HCID 59497772HCID 59497772, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-chloro-N-(trans-2-hydroxymethylcyclopentyl)benzenesulfonamide (290 mg, 1.0 mmol), cesium carbonate (652 mg, 2.0 mmol), and α-bromo-p-tolunitrile (253 mg, 1.2 mmol) in 2 mL dimethylformamide was stirred for 2 h. The reaction was diluted into 50 mL ethyl acetate and extracted with brine. The organic layer was concentrated and purified by flash chromatography on a 40 g silica gel column using a gradient of 20 to 70% ethyl acetate in hexane over 25 min. to give 4-chloro-N-(4-cyanobenzyl)-N-(trans-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (327 mg, 81%). 1H NMR (400 MHz, CDCl3) δ ppm 7.71 (2H, d, J=8.56 Hz), 7.57-7.63 (2H, m), 7.49 (3H, dd, J=10.83, 8.31 Hz), 4.64 (1H, d, J=16.62 Hz), 4.16 (1H, d, J=16.62 Hz), 3.99-4.12 (1H, m), 3.37-3.62 (2H, m), 1.99 (1H, t, J=6.17 Hz), 1.32-1.71 (7H, m). LC/MS R.T.=2.77 min; [M+H]+=404.12. HRMS [M+H]+ calc'd 405.1040, found 405.1054.

Workup

  1. extractionextracted with brine
  2. concentrationThe organic layer was concentrated
  3. custompurified by flash chromatography on a 40 g silica gel column
  4. customover 25 min.

Sources & evidence

ORD record
ord-47840d8cd2f944dcb37ebfcc2fd75cfd
Source dataset
uspto-grants-2011_07
Patent number
US07977362B2

Reaction notes

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