Water → (R)-2-Amino-N-benzyl-3-methoxypropionamide

HRID 1852048Notes

Reaction equation

HRID 1852048 reaction equation
[CH2:1]([NH:8][C:9](=[O:21])[C@H:10]([NH:13]C(=O)OC(C)(C)C)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].S(OC)(O[CH3:28])(=O)=O.O>ClCCl>[NH2:13][C@H:10]([CH2:11][O:12][CH3:28])[C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 46223140tert-butyl N-[(1R)-1-(benzylcarbamoyl)-2-hydroxyethyl]carbamate

Product 1

HCID 10104501(R)-2-Amino-N-benzyl-3-methoxypropionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Accordingly to a solution of the compound tert-butyl [(R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxoethyl]carbamate of Formula-XXI in dichloromethane, charged the phase transfer catalyst and cooled the reaction mass to −10° C. and charged dilute solution of sodium hydroxide. Maintaining the temperature at −10° C.-0° C. charged dimethyl sulfate and maintained the reaction under stirring for 3-5 hours. Charged water at the end of the reaction, stirred, separated the organic layer and extracted the aqueous layer with the dichloromethane. Combined the organic layer and acidified with concentrated hydrochloric acid. Charged water to the clear solution and stirred. Separated the aqueous layer and extracted the organic layer further with water. Combined the entire aqueous layer and adjusted the pH to 12 with aqueous sodium hydroxide solution. Extracted the aqueous layer with dichloromethane and separated the organic layer. Extracted the aqueous layer further with dichloromethane to ensure the complete extraction of the desired product. The organic layer is washed and concentrated to isolate the compound (2R)-2-amino-N-benzyl-3-methoxypropanamide of Formula-VIII.

Workup

  1. temperatureMaintaining the temperature at −10° C.-0° C.
  2. temperaturemaintained
  3. customthe reaction
  4. stirringstirred
  5. customseparated the organic layer
  6. extractionextracted the aqueous layer with the dichloromethane
  7. stirringCharged water to the clear solution and stirred
  8. customSeparated the aqueous layer
  9. extractionextracted the organic layer further with water
  10. extractionExtracted the aqueous layer with dichloromethane
  11. customseparated the organic layer
  12. extractionExtracted the aqueous layer further with dichloromethane
  13. extractionthe complete extraction of the desired product
  14. washThe organic layer is washed
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-df53dc5bf3794719bb71ad92eaaedf65
Source dataset
uspto-grants-2015_02
Patent number
US08957252B2

Reaction notes

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