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

HRID 2059885Notes

Reaction equation

[OH-].[Na+].[CH:3]1([N:6]([CH2:20][CH2:21][OH:22])[S:7]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH3:18])=[CH:12][C:11]=2[CH3:19])(=[O:9])=[O:8])[CH2:5][CH2:4]1.[C:23]([O:27][C:28](=[O:31])[CH2:29]Br)([CH3:26])([CH3:25])[CH3:24]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:3]1([N:6]([CH2:20][CH2:21][O:22][CH2:29][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:31])[S:7]([C:10]2[C:15]([CH3:16])=[CH:14][C:13]([O:17][CH3:18])=[CH:12][C:11]=2[CH3:19])(=[O:9])=[O:8])[CH2:4][CH2:5]1

Participants

Conditions

Temperature: 25 °C

Procedure

tetra-n-Butylammonium chloride (0.33 eq) and 35% sodium hydroxide solution (18 ml) were added to a solution of N-cyclopropyl-N-(2-hydroxyethyl)-4-methoxy-2,6-dimethylphenylsulfonamide (3.3 mmol) in toluene (18 ml), cooled to 0° C. tert-Butylbromoacetate (1.5 eq) was added slowly to this mixture at 0° C. On completion of the addition the mixture was stirred for 90 min at 25° C. until the reaction was complete. The organic phase was separated off, washed with water until a neutral pH was measured, dried over MgSO4, filtered and concentrated completely to obtain the desired product. Yield: 90%

Workup

additionwas added slowly to this mixture at 0° C
additionOn completion of the addition the mixture
customThe organic phase was separated off
washwashed with water until a neutral pH
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated completely

Sources & evidence

ORD record: ord-d47908948486495395945d089a19b03d
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278319B2

Reaction notes

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