Sodium Hydroxide → 2-(Methyl(p-tolylsulfonyl)amino)prop-2-enoic acid

HRID 1479817Notes

Reaction equation

O[CH2:2][C@H:3]([N:8]([CH3:19])[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4]([O:6]C)=[O:5].[OH-].[Na+]>O1CCOCC1>[CH3:19][N:8]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=[O:11])=[O:10])[C:3](=[CH2:2])[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 3E (1.4 g, 4.87 mmol) in dioxane (30 mL) was added with 20% NaOH aq. solution (30 mL) and the mixture was heated at 60° C. overnight. The organic solvent was removed under reduced pressure and the aqueous phase was acidified with 10% HCl and extracted with CH2Cl2 (3×50 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 4E as a pale yellow solid (0.8 g, 65% yield). 1HNMR (DMSO, 200 MHz) δ 2.81 (s, 3H), 2.88 (s, 3H), 5.46 (s, 1H), 6.02 (s, 2H), 7.41 (d, 2H, J=7.8), 7.66 (d, 2H, H=8), 13.01 (bs, 1H).

Workup

customThe organic solvent was removed under reduced pressure
extractionextracted with CH2Cl2 (3×50 mL)
dry with materialThe combined organic phases were dried over Na2SO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-adf4cef768b9476e9b26d8076352ea68
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

Loading…