Methanol → HCID 178445744, compound

HRID 1036466Notes

Reaction equation

HRID 1036466 reaction equation
O.[OH-].[Li+].O.C[O:6][C:7](=[O:39])[CH2:8][CH2:9][CH:10]([C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:28][C@H:29]3[CH2:34][CH2:33][C@H:32]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:31][CH2:30]3)[C:20]=2[C:24]([F:27])([F:26])[F:25])[CH:15]=1)[N+:11]([O-:13])=[O:12].CO.O1CCCC1>>[C:35]([C@H:32]1[CH2:31][CH2:30][C@H:29]([O:28][C:19]2[C:20]([C:24]([F:25])([F:26])[F:27])=[C:21]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([CH:10]([N+:11]([O-:13])=[O:12])[CH2:9][CH2:8][C:7]([OH:39])=[O:6])[CH:23]=[CH:22]3)[CH2:34][CH2:33]1)([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178500093HCID 178500093, compound

Product 1

HCID 178445744HCID 178445744, compoundYield 73.3%

Procedure

A 2 M solution of lithium hydroxide, monohydrate in water (1.00 mL, 2.00 mmol) was added to a solution of 4-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-4-nitro-butyric acid methyl ester (0.114 g, 0.230 mmol) in methanol (1.00 mL, 24.7 mmol) and tetrahydrofuran (1.00 mL, 12.3 mmol). The mixture was stirred at room temperate. After 2 h, HPLC analysis showed that the reaction was complete. The mixture was concentrated to dryness under reduced pressure then dissolved in methylene chloride and partitioned between 1N HCl aqueous solution. The organic phase was then dried over MgSO4, filtered, concentrated and purified by flash chromatography (0-5% MeOH in methylene chloride) to give 81.2 mg of the title compound (73% yield).

Workup

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. dissolutionthen dissolved in methylene chloride
  3. custompartitioned between 1N HCl aqueous solution
  4. dry with materialThe organic phase was then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography (0-5% MeOH in methylene chloride)

Sources & evidence

ORD record
ord-f4f7c02384bf479fb07ef4195bcedcc3
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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