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

HRID 62577Notes

Reaction equation

HRID 62577 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 68.4%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
60 °C

Procedure

N-Acetyl-D-serine methyl ester (1.0 g, 0.0062 mole) was dissolved in benzylamine (1.32 g, 0.0124 mole) at 0-5° C. To this was added triethylamine (0.125 g, 0.00124 mole) at 0-5° C. The reaction mixture was heated and stirred at 60° C. for 12 hr, cooled to room temperature, 20 ml methyl tert-butyl ether added and stirred for 3 hr. The product was filtered and dried under vacuum to obtain (R)-2-acetamido-N-benzyl-3-hydroxy-propionamide. (1.0 g, Yield: 68.4%, HPLC:94.8%, Chiral HPLC: 81.2%),

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturecooled to room temperature
  3. stirringstirred for 3 hr
  4. filtrationThe product was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0824146e65c64c0c84597fe69b3f626d
Source dataset
uspto-grants-2016_09
Patent number
US09447024B1

Reaction notes

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