3-azido-1-benzyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one → (3-Amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetic acid

HRID 2418720노트

반응식

HRID 2418720 반응식
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([CH2:15][C:16]([O:18]CC2C=CC=CC=2)=[O:17])[C:5]1=[O:26])=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=2[N:6]([CH2:15][C:16]([OH:18])=[O:17])[C:5]1=[O:26]

참가 물질

4

반응물 1

HCID 132434973-azido-1-benzyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one

생성물 1

HCID 13243494(3-Amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)acetic acid

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매2회

실험 절차

A solution of 3-azido-1-benzyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one (14.0 g, 0.04 mol) in ethanol (300 ml) was hydrogenated for 25 hours on a Parr shaker at 45 psi at room temperature using 5% Pd-C (2.0 g) as catalyst. The catalyst was filtered off and the solvent removed under reduced pressure. The residue was dissolved in water (500 ml) and the solution extracted with dichloromethane (2×400 ml). The aqueous solution was filtered, and evaporated under reduced pressure. Ethanol (50 mol) was added and the solution evaporated under reduced pressure. More ethanol (50 ml) was added, and the evaporation repeated. The residue was recrystallized from ethanol/ethyl acetate to give 3-amino-1-carboxymethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 147°-50°.

후처리

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was dissolved in water (500 ml)
  4. extractionthe solution extracted with dichloromethane (2×400 ml)
  5. filtrationThe aqueous solution was filtered
  6. customevaporated under reduced pressure
  7. customthe solution evaporated under reduced pressure
  8. additionMore ethanol (50 ml) was added
  9. customthe evaporation
  10. customThe residue was recrystallized from ethanol/ethyl acetate

출처 및 근거

ORD 기록
ord-39a11d9ae72d41fdb61f87cd055cc78d
출처 데이터셋
uspto-grants-1984_09
특허 번호
US04473575

반응 노트

불러오는 중…