Methane → (2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

HRID 273479Notes

Reaction equation

HRID 273479 reaction equation
C([O:8][C:9](=[O:22])[C@H:10]([CH3:21])[NH:11][C@H:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][CH2:14][CH3:15])C1C=CC=CC=1.C.[H][H]>C(O)C>[CH2:19]([O:18][C:16]([C@@H:12]([NH:11][C@H:10]([C:9]([OH:22])=[O:8])[CH3:21])[CH2:13][CH2:14][CH3:15])=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 297MethaneHCID 11493275N-[(S)-1-Carbethoxybutyl]-(S)-alanine Benzyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 10015159(2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acidYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-[1-(S)-ethoxycarbonyl-1-butyl]-(S)-alanine benzyl ester (14.5 g, as obtained in Step-I) in ethanol (150 ml) was hydrogenated in the presence of 10% palladised charcoal (0.8 g) under 40-45 psi hydrogen pressure for 1.5 to 2 hrs. The reaction mixture was concentrated under reduced pressure to give an oil. Crystallization from a mixture of acetonitrile and ethanol (1:3) gave 6.1 g the title compound

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give an oil
  3. customCrystallization
  4. additionfrom a mixture of acetonitrile and ethanol (1:3)

Sources & evidence

ORD record
ord-a9b05529552d4269b5cbb7a76c665f81
Source dataset
uspto-grants-2008_11
Patent number
US07456296B2

Reaction notes

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