Hydrochloric Acid → 4-[3-Pentyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-Naphthalen-2-yl)-Ureido]-Benzoic Acid

HRID 1760840Notes

Reaction equation

[CH2:1]([N:6]([C:21]1[CH:30]=[CH:29][C:28]2[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=2[CH:22]=1)[C:7](=[O:20])[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[K+].C1COCC1.Cl>C(O)C.O>[CH2:1]([N:6]([C:21]1[CH:30]=[CH:29][C:28]2[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:33])([CH3:34])[C:23]=2[CH:22]=1)[C:7](=[O:20])[NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 45 °C

Procedure

A solution of ethyl 4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (37) (360 mg, 0.77 mmole) in 10 mL ethanol was treated with 430 mg of potassium hydroxide in 2 mL water. THF (2 mL) was added and the mixture was heated to 45° C. for two hours. The reaction mixture was diluted with 10 mL water, the pH adjusted to 2 with concentrated HCl and then extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, to give a pale yellow solid. The product was purified by trituration in pentane and 280 mg of 4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (27) were obtained as a white solid. M.P.: 184-186° C.

Workup

extractionextracted with three 25 mL portions of ethyl acetate
dry with materialThe combined organic extracts were dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give a pale yellow solid
customThe product was purified by trituration in pentane

Sources & evidence

ORD record: ord-15875df89ccc486fb9e16083cb76d2db
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06844466B2

Reaction notes

Loading…