Water → (2R)-2-azido-N-benzyl-3-hydroxypropanamide

HRID 1852049Notes

Reaction equation

HRID 1852049 reaction equation
[CH2:1]([NH:8][C:9](=[O:14])[C@@H:10](Br)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+].O.C([O-])(O)=O.[Na+]>CN(C)C=O>[N:15]([C@H:10]([CH2:11][OH:12])[C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:14])=[N+:16]=[N-:17]

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 56640202(2S)-N-benzyl-2-bromo-3-hydroxypropanamide

Product 1

HCID 56640203(2R)-2-azido-N-benzyl-3-hydroxypropanamideYield 99.62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
52.5 °C

Procedure

To a reaction flask was charged (2S)-N-benzyl-2-bromo-3-hydroxypropanamide (80.0 g) and sodium azide (30.23 g) in N,N-dimethylformamide (480 ml) and raised the temperature to 50-55° C. and maintained for 4-5 hours. Stopped heating and cooled the reaction mixture to 20-25° C. and charged DM water (400 ml), adjusted pH of the reaction mixture to 9-9.5 using 5% NaHCO3 solution. Extracted the reaction mass with ethyl acetate (1×800 ml, 2×280 ml). Separated the organic layer and combined all ethyl acetate layers, washed with saturated ammonium chloride solution (2×240 ml). Concentrated the solvent ethyl acetate under reduced pressure to get oily compound of (2R)-2-azido-N-benzyl-3 -hydroxypropanamide.

Workup

  1. temperaturemaintained for 4-5 hours
  2. temperatureStopped heating
  3. temperaturecooled the reaction mixture to 20-25° C.
  4. extractionExtracted the reaction mass with ethyl acetate (1×800 ml, 2×280 ml)
  5. customSeparated the organic layer
  6. washwashed with saturated ammonium chloride solution (2×240 ml)
  7. concentrationConcentrated the solvent ethyl acetate under reduced pressure

Sources & evidence

ORD record
ord-f5b4b7af162e46a498bd6b24ac3e37c7
Source dataset
uspto-grants-2015_02
Patent number
US08957252B2

Reaction notes

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