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

HRID 62575Notes

Reaction equation

HRID 62575 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 75%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
65 °C

Procedure

N-Acetyl-D-serine methyl ester (1.0 g, 0.0062 mole) was dissolved in benzylamine (6.64 g, 0.062 mole) at 0-5° C. The reaction mixture was heated and stirred at 65° C. for 12 hr. The excess benzylamine was removed by distillation under vacuum at 90° C. to get a thick white solid. To this was added 10 ml of methyl tert-butyl ether and stirred for 2 hr at room temperature. The product was filtered and dried under vacuum to obtain (R)-2-acetamido-N-benzyl-3-hydroxy-propionamide (1.09 g, Yield 75%, HPLC: 92%, Chiral HPLC: 78%).

Workup

  1. temperatureThe reaction mixture was heated
  2. customThe excess benzylamine was removed by distillation under vacuum at 90° C.
  3. customto get a thick white solid
  4. stirringstirred for 2 hr at room temperature
  5. filtrationThe product was filtered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d1d11f6805674c38ac83dd237d015e75
Source dataset
uspto-grants-2016_09
Patent number
US09447024B1

Reaction notes

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