Methane → 2-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid

HRID 1295347Notes

Reaction equation

HRID 1295347 reaction equation
C([O:3][C:4]([C:6]12[CH2:11][CH:10]1[CH2:9][N:8]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:7]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:5])C.C>[OH-].[Na+].C(O)C>[C:22]1([CH:7]2[N:8]([S:12]([C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)(=[O:14])=[O:13])[CH2:9][CH:10]3[C:6]2([C:4]([OH:5])=[O:3])[CH2:11]3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 297MethaneHCID 589073302-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester2×

Product 1

HCID 589073232-Phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of racemic 2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid ethyl ester (Intermediate 1) in 400 mL 10% NaOH and 80 mL ethanol was refluxed for 6 hours. The solution was allowed to cool, treated with decolorizing charcoal, and filtered thru supercel. The ethanol was evaporated at reduced pressure and the residual solution was cooled in an ice bath and acidified with concentrated HCl to pH 1. The product precipitated and was granulated for one hour, then collected by filtration to give 2-phenyl-3-(toluene-4-sulfonyl)-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid as a white solid (19.38 g, quantitative).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customThe ethanol was evaporated at reduced pressure
  4. temperaturethe residual solution was cooled in an ice bath
  5. customThe product precipitated
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-477410f3d7454970aea97d53e375346b
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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