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

HRID 62576Notes

Reaction equation

HRID 62576 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(N(CC)CC)C>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

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 45082407HCID 45082407, compound

Product 1

HCID 10889901(R)-N-Benzyl-2-acetamido-3-hydroxypropionamideYield 93%

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. To this triethylamine (3.13 g, 0.031 mole) was added at 0-5° C. The reaction mixture was allowed to cool to room temperature and stirred for 12 hr. To the thick colorless precipitate formed 300 ml methyl tert-butyl ether was added and stirred for 6 hr. The product was filtered and dried under vacuum to obtain (R)-2-acetamido-N-benzyl-3-hydroxy-propionamide (34.03 g, Yield: 93%, HPLC: 98.9, Chiral HPLC: 98.8%)

Workup

  1. additionwas added
  2. stirringstirred for 6 hr
  3. filtrationThe product was filtered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-158524a3904b439bb649f21e6c685020
Source dataset
uspto-grants-2016_09
Patent number
US09447024B1

Reaction notes

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