Potassium Hydroxide → HCID 178484023, compound

HRID 967135Notes

Reaction equation

HRID 967135 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH3:14])[CH2:8][CH2:7]1.[OH-].[K+]>C(O)C>[C:18]([O:17][C:15]([N:13]([CH2:12][C@H:9]1[CH2:10][CH2:11][C@H:6]([CH2:5][CH2:4][C:3]([OH:22])=[O:2])[CH2:7][CH2:8]1)[CH3:14])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 178500455HCID 178500455, compound

Product 1

HCID 178484023HCID 178484023, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.990 g (3.16 mmol) trans-3-{4-[(tert-butoxycarbonyl-methyl-amino)-methyl]-cyclohexyl}-propionic acid methyl ester and 660 mg potassium hydroxide were dissolved in 5.0 ml of ethanol and the reaction mixture heated at reflux for 3 hours. It was then evaporated, subsequently poured into 50 ml of an ice/water mixture, acidified with aqueous hydrochloric acid to pH 5 and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were dried over magnesium sulfate and evaporated under reduced pressure giving 0.900 g (95%) trans-3-{4-[(tert-butoxycarbonyl-methyl-amino)-methyl]-cyclohexyl}-propionic acid as colorless viscous oil, MS: 299 (M+).

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 3 hours
  3. customIt was then evaporated
  4. additionsubsequently poured into 50 ml of an ice/water mixture
  5. extractionextracted 3 times with 50 ml of dichloromethane
  6. dry with materialThe combined dichloromethane phases were dried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-56ca7c613a7b414882701777418762a8
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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