Water → HCID 178447445, compound

HRID 1036525Notes

Reaction equation

HRID 1036525 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][CH2:5][C:6]([N+:29]([O-:31])=[O:30])([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([C:25]([F:28])([F:27])[F:26])[CH2:21][CH2:20]3)[CH:14]=2)[CH:9]=1)[CH3:7].[OH-].[Li+].O>CO.O1CCCC1>[N+:29]([C:6]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C@H:19]3[CH2:20][CH2:21][C@H:22]([C:25]([F:26])([F:27])[F:28])[CH2:23][CH2:24]3)[CH:14]=2)[CH:9]=1)([CH3:7])[CH2:5][CH2:4][C:3]([OH:32])=[O:2])([O-:31])=[O:30]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 178500165HCID 178500165, compound

Product 1

HCID 178447445HCID 178447445, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitro-4-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid methyl ester (0.098 g, 0.22 mmol) in methanol (1.00 mL, Fisher) and tetrahydrofuran (1.00 mL, Acros) was added 2 M lithium hydroxide in water (1.00 mL, 2.00 mmol). The mixture was stirred at room temperature. After 2 hours, the mixture was concentrated under vacuum. The resulting product was diluted in methylene chloride and washed with 1N HCl. The combined organic phases were dried over Na2SO4, filtered and concentrated to give the product in 99 mg yield (100%).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. additionThe resulting product was diluted in methylene chloride
  3. washwashed with 1N HCl
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the product in 99 mg
  8. customyield (100%)

Sources & evidence

ORD record
ord-105b11e2eba840828d998e7fba17b2cb
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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