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

HRID 1760831Notes

Reaction equation

HRID 1760831 reaction equation
[CH2:1]([N:5]([C:20]1[CH:29]=[CH:28][C:27]2[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=2[CH:21]=1)[C:6](=[O:19])[NH:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Li+]>CO.C1COCC1.O>[CH2:1]([N:5]([C:20]1[CH:29]=[CH:28][C:27]2[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:32])([CH3:33])[C:22]=2[CH:21]=1)[C:6](=[O:19])[NH:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 22596834Ethyl 4-[3-butyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate

Product 1

HCID 225968404-[3-Butyl-3-(5,5,8,8-Tetramethyl-5,6,7,8-Tetrahydro-Naphthalen-2-yl)-Ureido]-Benzoic AcidYield 28%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 4-[3-butyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (11) (131 mg, 0.29 mmole) in 15 mL methanol, 5 mL of THF and 5 mL of water was treated with 62 mg of lithium hydroxide (5 eq.) and stirred at room temperature for eight hours. The mixture was concentrated in vacuo and the residue was acidified with concentrated HCl solution. The mixture was then extracted with three portions of 20 mL of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow solid which was purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes+drops of acetic acid) to provide 34 mg (28%) of 4-[3-butyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (5) as a pale yellow solid. MS (EI): (M++1) 423.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionThe mixture was then extracted with three portions of 20 mL of ethyl acetate
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid which
  7. customwas purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes+drops of acetic acid)

Sources & evidence

ORD record
ord-a46c72cb9d474e0c87642493c4a73224
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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