Sodium Hydroxide → trans-2-(trans-2-Methylcyclohexylcarbamoyl)-cyclopropanecarboxylic acid

HRID 501281Notes

Reaction equation

HRID 501281 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:7][C@H:6]1[C:8](=[O:17])[NH:9][CH:10]1[CH2:15][CH2:14][CH:13](C)[CH2:12][CH2:11]1)=[O:4].[OH-].[Na+].CO.O1CCOC[CH2:23]1>>[CH3:23][C@@H:15]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:9][C:8]([C@@H:6]1[CH2:7][C@H:5]1[C:3]([OH:2])=[O:4])=[O:17]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21966525Dioxane MethanolHCID 68456814trans-2-(4-Methyl-cyclohexylcarbamoyl)-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 68455212trans-2-(trans-2-Methylcyclohexylcarbamoyl)-cyclopropanecarboxylic acidYield 87%

Procedure

Stir a solution of trans-2-(4-methyl-cyclohexylcarbamoyl)-cyclopropane-carboxylic acid monomethyl ester (Example 11a) (4.5 g, 19.8 mmol), 5N NaOH (40 mL) and MeOH/dioxane overnight. Concentrate the reaction mixture under vacuum, cool the resulting solution and acidify to pH 5. Collect the precipitate, wash (H2O) and dry under vacuum at 40° C. to obtain 3.7 g (87%) of solid.

Workup

  1. concentrationConcentrate the reaction mixture under vacuum
  2. temperaturecool the resulting solution
  3. customCollect the precipitate
  4. washwash (H2O)
  5. customdry under vacuum at 40° C.

Sources & evidence

ORD record
ord-1255e7da9b914501b6bd5033fd21cb06
Source dataset
uspto-grants-2010_08
Patent number
US07772252B2

Reaction notes

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