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

HRID 1852048노트

반응식

HRID 1852048 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-df53dc5bf3794719bb71ad92eaaedf65
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957252B2

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