Hydrochloric Acid → HCID 22596838, compound

HRID 1760844Notes

Reaction equation

HRID 1760844 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][C:13]([N:15]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:16]1[CH:25]=[CH:24][C:23]2[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]([CH3:29])([CH3:28])[C:18]=2[CH:17]=1)=[O:14])[C:5]([O:7]C)=[O:6].O.[OH-].[Li+].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][C:13]([N:15]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:16]1[CH:25]=[CH:24][C:23]2[C:22]([CH3:26])([CH3:27])[CH2:21][CH2:20][C:19]([CH3:28])([CH3:29])[C:18]=2[CH:17]=1)=[O:14])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 22596830HCID 22596830, compound

Product 1

HCID 22596838HCID 22596838, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-fluoro-4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoate (17 mg) in 10 mL THF/3 mL methanol/3 mL water was treated with lithium hydroxide hydrate (20 mg). The mixture was stirred at room temperature for two hours. The mixture was diluted with 5 mL water and the pH was adjusted to 2 with conc. HCl. The mixture was extracted with three 10 mL portions of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo, giving a brown solid. The product was purified by trituration in hexanes, yielding 12 mg 3-fluoro4-[3-pentyl-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ureido]-benzoic acid as a yellow solid. M.P. 151-157° C.

Workup

  1. extractionThe mixture was extracted with three 10 mL portions of ether
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customgiving a brown solid
  6. customThe product was purified by trituration in hexanes

Sources & evidence

ORD record
ord-d7f20c75f62e4df983e92e24f5df3772
Source dataset
uspto-grants-2005_01
Patent number
US06844466B2

Reaction notes

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