Hydrochloric Acid → HCID 10225152, compound

HRID 1759778Notes

Reaction equation

HRID 1759778 reaction equation
O.[OH-].[Li+].[CH2:4]([O:6][CH2:7][CH2:8][N:9]([C:23]1[CH:32]=[CH:31][C:30]2[C:29]([CH3:34])([CH3:33])[CH2:28][CH2:27][C:26]([CH3:36])([CH3:35])[C:25]=2[CH:24]=1)[C:10](=[O:22])[NH:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)[CH3:5].CO.Cl>C1COCC1.O>[CH2:4]([O:6][CH2:7][CH2:8][N:9]([C:23]1[CH:32]=[CH:31][C:30]2[C:29]([CH3:34])([CH3:33])[CH2:28][CH2:27][C:26]([CH3:35])([CH3:36])[C:25]=2[CH:24]=1)[C:10](=[O:22])[NH:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 22600036HCID 22600036, compound

Product 1

HCID 10225152HCID 10225152, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (0.5 g) was added to a solution of methyl 4-[3-(2-ethoxy-ethyl)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (39) (520 mg) dissolved in 20 mL THF, 5 mL methanol and 5 mL and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was diluted with 20 mL water, the pH was adjusted to 2 with concentrated HCl and extracted with three 25 mL portions of ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give 400 mg of 4-[3-(2-ethoxy-ethyl)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid (33) as a colorless oil, which crystallized upon addition of hexanes. M.P.: 82-85° C.

Workup

  1. extractionextracted with three 25 mL portions of ethyl acetate
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23904a103b1c4a83984a342c27fdae21
Source dataset
uspto-grants-2005_01
Patent number
US06838472B2

Reaction notes

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