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(2R)-2-azido-N-benzyl-3-hydroxypropanamide → (2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamide

HRID 1852050
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HRID 1852050 반응식
[N:1]([C@H:4]([CH2:15][OH:16])[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])=[N+]=[N-].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C@H:4]([CH2:15][OH:16])[C:5]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]
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참가 물질

5

반응물 2

HCID 56640203(2R)-2-azido-N-benzyl-3-hydroxypropanamideHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 10655432(2R)-2-Amino-3-hydroxy-N-(phenylmethyl)propanamide

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

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온도
27.5 °C

실험 절차

In an autoclave charged (2R)-2-azido-N-benzyl-3-hydroxypropanamide (68.0 gms) in ethyl acetate (680 ml). Charged catalyst 5% Pd-C (6.85 gms) and closed the autoclave. Applied 3.8 kg Hydrogen pressure maintaining temperature at 25-30° C. and maintained the reaction mixture at 25-30° C. for 1.0 hour. After completion of the reaction, released Hydrogen pressure and flushed the autoclave with Nitrogen gas. Filtered the reaction mass through hyflo bed and washed hyflo bed with ethyl acetate. Concentrated filtrate under reduced pressure at 30-35° C. till two volumes of ethyl acetate remains in the reaction mixture. Removed vacuum and cooled the reaction mass to 0-5° C. and maintained for 2.0 hours. The reaction mass was filtered and washed with cold ethyl acetate (2×40 ml). Dried the product (2R)-2-amino-N-benzyl-3-hydroxypropanamide under vacuum at 25-30° C. till constant weight.

후처리

  1. customAfter completion of the reaction
  2. customflushed the autoclave with Nitrogen gas
  3. filtrationFiltered the reaction mass through hyflo bed
  4. washwashed
  5. customat 30-35° C.
  6. customRemoved vacuum
  7. temperaturecooled the reaction mass to 0-5° C.
  8. temperaturemaintained for 2.0 hours
  9. filtrationThe reaction mass was filtered
  10. washwashed with cold ethyl acetate (2×40 ml)
  11. dry with materialDried the product (2R)-2-amino-N-benzyl-3-hydroxypropanamide under vacuum at 25-30° C. till constant weight

출처 및 근거

ORD 기록
ord-086fcebc55394129afee68dbab3c5fc5
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957252B2

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