Sodium Hydroxide → tert-butyl 2-(2-(4-methoxy-N,2,6-trimethylphenyl-sulfonamido)ethoxy)acetate

HRID 2388656Notes

Reaction equation

HRID 2388656 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:18])[S:5]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=1[CH3:17])(=[O:7])=[O:6].[OH-].[Na+].[C:21]([O:25][C:26](=[O:29])[CH2:27]Br)([CH3:24])([CH3:23])[CH3:22]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].C1(C)C=CC=CC=1>[CH3:16][O:15][C:11]1[CH:12]=[C:13]([CH3:14])[C:8]([S:5]([N:4]([CH2:3][CH2:2][O:1][CH2:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:29])[CH3:18])(=[O:7])=[O:6])=[C:9]([CH3:17])[CH:10]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 51712110N-(2-Hydroxyethyl)-4-methoxy-N,2,6-trimethylbenzenesulfonamide

Product 1

HCID 59597898tert-butyl 2-(2-(4-methoxy-N,2,6-trimethylphenyl-sulfonamido)ethoxy)acetate

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

n-Bu4NCl (39 g, 140.1 mmol) was added to a solution of N-(2-hydroxyethyl)-4-methoxy-N,2,6-trimethylbenzenesulfonamide (116 g, 424.4 mmol) in toluene (750 ml) and the mixture was cooled to 0° C. Aqueous 35% strength NaOH solution (1,000 ml) was then added. Bromoacetic acid tert-butyl ester (93 ml, 636.6 mmol) was then added dropwise to the reaction mixture and the mixture was stirred at room temperature for 2 hours. The organic phase was separated off, washed with water (3×750 ml), dried over Na2SO4 and concentrated in vacuo. Purification was carried out by chromatography on silica gel (heptane/ethyl acetate 4:1). The yield was 124.6 g (76%).

Workup

  1. customThe organic phase was separated off
  2. washwashed with water (3×750 ml)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-46b59f7f72f64c83af3b7365f97053e9
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

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