Sodium Hydroxide → tert-butyl 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)ethoxy)acetate

HRID 2388661Notes

Reaction equation

HRID 2388661 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH:16]1[CH2:18][CH2:17]1)[CH2:13][CH2:14][OH:15])(=[O:11])=[O:10].[OH-].[Na+].Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>ClCCl.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9]([N:12]([CH2:13][CH2:14][O:15][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:16]1[CH2:18][CH2:17]1)(=[O:11])=[O:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 579162662-chloro-N-cyclopropyl-N-(2-hydroxyethyl)-6-methylbenzenesulfonamide

Product 1

HCID 57916276tert-butyl 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)ethoxy)acetateYield 70%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of 2-chloro-N-cyclopropyl-N-(2-hydroxyethyl)-6-methylbenzenesulfonamide (1 eq.) in dichloromethane (15 ml) was added tetrabutylammonium chloride (0.1 eq.) and 35% sodium hydroxide solution (15 ml) at 0° C. tert-Butyl 2-bromoacetate (1.2 eq.) was added dropwise to this cold reaction mixture maintaining the same temperature. After addition was complete, the reaction mixture was stirred at room temperature for 16 h (monitored by TLC). It was diluted with dichloromethane and the organic layer was washed with water and brine and finally dried over sodium sulfate. Evaporation of the organic layer under reduced pressure gave the crude product which was purified by column chromatography (20% ethyl acetate in hexane). Yield: 70%

Workup

  1. additionwas added dropwise to this cold reaction mixture
  2. temperaturemaintaining the same temperature
  3. additionAfter addition
  4. washthe organic layer was washed with water and brine
  5. dry with materialfinally dried over sodium sulfate
  6. customEvaporation of the organic layer under reduced pressure

Sources & evidence

ORD record
ord-6cf1f059ab4643b38a5d12a6e518c398
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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