Benzylamine → (R)-N-Benzyl-2-acetamido-3-hydroxypropionamide

HRID 62574Notes

Reaction equation

HRID 62574 reaction equation
CO[C:3](=[O:11])[C@@H:4]([CH2:9][OH:10])[NH:5][C:6](=[O:8])[CH3:7].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OC)(C)(C)C>[C:6]([NH:5][C@H:4]([CH2:9][OH:10])[C:3]([NH:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 45082407HCID 45082407, compound

Product 1

HCID 10889901(R)-N-Benzyl-2-acetamido-3-hydroxypropionamideYield 82%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

N-Acetyl-D-serine methyl ester (25 g, 0.155 mole) was dissolved in benzylamine (33.2 g, 0.3101 mole) at 0-5° C. The reaction mixture was allowed to room temperature and stirred for 12 hr. To the thick colorless precipitate formed was added 300 ml methyl tert-butyl ether and stirred for 6 hr. The product was filtered and dried under vacuum to obtain (R)-2-acetamido-N-benzyl-3-hydroxy-propionamide (30.0 g, Yield: 82%, HPLC: 98.9, Chiral HPLC: 96.2%).

Workup

  1. customwas allowed to room temperature
  2. customTo the thick colorless precipitate formed
  3. stirringstirred for 6 hr
  4. filtrationThe product was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-fd174bc59cba422bafbe736ba1f9d9f6
Source dataset
uspto-grants-2016_09
Patent number
US09447024B1

Reaction notes

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