Ammonium formate → (R)-5-(2-Amino-1-(tert-butyldimethylsilyloxy)ethyl)-8-hydroxyquinolin-2(1H)-one formate

HRID 1472739노트

반응식

HRID 1472739 반응식
[N:1]([CH2:4][C@@H:5]([C:14]1[CH:23]=[CH:22][C:21]([O:24]CC2C=CC=CC=2)=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18](=[O:32])[NH:19]2)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[N+]=[N-].[CH:33]([O-:35])=[O:34].[NH4+]>[Pd].CO>[CH:33]([OH:35])=[O:34].[NH2:1][CH2:4][C@@H:5]([C:14]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]2[C:15]=1[CH:16]=[CH:17][C:18](=[O:32])[NH:19]2)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 58505233(R)-5-(2-Azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one

생성물 1

HCID 71093302(R)-5-(2-Amino-1-(tert-butyldimethylsilyloxy)ethyl)-8-hydroxyquinolin-2(1H)-one formate수율 86%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

Palladium on activated carbon (0.4 g, 10% w/w) was added to a suspension of (R)-5-(2-azido-1-(tert-butyldimethylsilyloxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one (2.05 g, 4.60 mmol) and ammonium formate (2.87 g, 63 mmol) in methanol (50 mL). The reaction mixture was heated at 80° C. for 1 hour and then filtered through celite, washing with water. The reaction mixture was concentrated under reduced pressure. The resultant solid was washed with water, triturated with ethyl acetate and collected by filtration to afford the title compound (1.32 g, 86%).

후처리

  1. filtrationfiltered through celite
  2. washwashing with water
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washThe resultant solid was washed with water
  5. customtriturated with ethyl acetate
  6. filtrationcollected by filtration

출처 및 근거

ORD 기록
ord-aa4cb0be25d14da4abf8ca9ec63e4b7b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012644B2

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