Sodium Hydroxide → HCID 86651841, compound

HRID 1465450Notes

Reaction equation

HRID 1465450 reaction equation
[CH2:1]([S:3]([NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23]C)=[O:22])=[CH:16][CH:15]=2)[N:11]=1)(=[O:5])=[O:4])[CH3:2].[OH-].[Na+]>O1CCOCC1>[CH2:1]([S:3]([NH:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:18][CH:19]=2)[N:11]=1)(=[O:4])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86651840HCID 86651840, compound

Product 1

HCID 86651841HCID 86651841, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl [4-(2-{2-[(ethylsulfonyl)amino]-1,3-thiazol-4-yl}ethyl)phenyl]acetate (1.74 g, 4.72 mmol) in dioxane (17.4 ml) was added at 0° C. 1M aqueous sodium hydroxide solution (11.8 ml, 11.8 mmol), and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure, and water (20 ml) was added. After cooling to 0° C., 1M hydrochloric acid (16 ml) was added dropwise with stirring. After stirring at 0° C. for 30 mins, the precipitate was collected by filtration, washed with water and dried under reduced pressure to give [4-(2-{2-[(ethylsulfonyl)amino]-1,3-thiazol-4-yl}ethyl)phenyl]acetic acid (1.66 g, yield 99%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water (20 ml)
  2. additionwas added
  3. addition1M hydrochloric acid (16 ml) was added dropwise
  4. stirringAfter stirring at 0° C. for 30 mins
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-0f1b460d67f84e0fac12aea9521b2490
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

Loading…