HCID 10783870, compound → n-Boc-n-cyclohexylglycine

HRID 1940491Notes

Reaction equation

HRID 1940491 reaction equation
C([O:8][C:9](=[O:25])[CH2:10][N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)C1C=CC=CC=1>C(O)C>[C:18]([N:11]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:10][C:9]([OH:25])=[O:8])([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

Participants

3

Reactant 1

HCID 10783870HCID 10783870, compound

Product 1

HCID 10563100n-Boc-n-cyclohexylglycineYield 86.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Boc-N-(cyclohexyl)glycine benzyl ester (14.0 g, 40 mmol) was dissolved in 240 mL anhydrous ethanol, flushed with dry nitrogen and combined carefully under inert atmosphere with 1.5 g of 10% palladium on carbon. Using a Parr apparatus the nitrogen atmosphere was replaced with hydrogen (43 P.S.I.) and the mixture was shaken over 24 hours at room temperature. The mixture was purged with nitrogen and the catalyst and solids were removed by filtration through a pad of celite. The filtrate was concentrated by rotary evaporation and the residue was taken up in 300 mL of ethyl acetate. The ethyl acetate layer was extracted with 150 mL of 1N sodium hydroxide solution. The basic solution was acidified in an ice bath to pH 3 with 1N hydrochloric acid solution. The acid solution was extracted with ethyl acetate (3×100 mL). This solution was washed with saturated sodium chloride solution and concentrated in vacuo to a colorless oil which was further dried under high vacuum. The resulting glass/solid was triturated with hexane, which after filtration and drying provided the title compound (8.89 g) as a colorless powder. M.P. 103-104 C (uncorr.) Anal. (C13H23NO4) C, H, N; C: calcd., 60.68; found, 60.77 H; calcd., 9.01; found, 9.20. N: calcd., 5.44; found, 5.44.

Workup

  1. customflushed with dry nitrogen
  2. customThe mixture was purged with nitrogen
  3. customthe catalyst and solids were removed by filtration through a pad of celite
  4. concentrationThe filtrate was concentrated by rotary evaporation
  5. extractionThe ethyl acetate layer was extracted with 150 mL of 1N sodium hydroxide solution
  6. customThe basic solution was acidified in an ice bath to pH 3 with 1N hydrochloric acid solution
  7. extractionThe acid solution was extracted with ethyl acetate (3×100 mL)
  8. washThis solution was washed with saturated sodium chloride solution
  9. concentrationconcentrated in vacuo to a colorless oil which
  10. customwas further dried under high vacuum
  11. customThe resulting glass/solid was triturated with hexane, which
  12. filtrationafter filtration
  13. customdrying

Sources & evidence

ORD record
ord-3542683dfda3417ca38e93b60452f6d4
Source dataset
uspto-grants-1997_12
Patent number
US05700779

Reaction notes

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