Benzylamine → HCID 15870829, compound

HRID 582896Notes

Reaction equation

HRID 582896 reaction equation
[O:1]1[C@H:6]([CH2:7][CH3:8])[C@H:2]1[C:3]([OH:5])=[O:4].[OH-].[Na+].[CH2:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[CH2:11]([NH:18][C@H:2]([C@H:6]([OH:1])[CH2:7][CH3:8])[C:3]([OH:5])=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 55299097HCID 55299097, compound2×

Product 1

HCID 15870829HCID 15870829, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 14.2 g (0.05 mol) of the (2S,3R)-2,3-epoxypentanoic acid obtained in (4) above were added 500 ml of water and 6.4 g (0.16 mol) of sodium hydroxide, and 42.6 g (0.15 mol) of benzylamine (VI) was added thereto, followed by refluxing for 8 hours. Water was evaporated, and the concentrate was adjusted to pH 5 to 6 with diluted hydrochloric acid and extracted with 500 ml of ethyl acetate. After drying, ethyl acetate was removed by evaporation to yield 8.36 g (0.0375 mol, 75%) of the title compound. Optical rotation [α]D25 =+12.84° (c=0.1, CHCl3 :CH3OH=1:1 by volume)

Workup

  1. additionwas added
  2. temperatureby refluxing for 8 hours
  3. customWater was evaporated
  4. extractionextracted with 500 ml of ethyl acetate
  5. customAfter drying
  6. customethyl acetate was removed by evaporation

Sources & evidence

ORD record
ord-f884c2c488a54618b7705398a97feae0
Source dataset
uspto-grants-1999_07
Patent number
US05925792

Reaction notes

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