Ethyl Acetate → 5-[(R)-2-{Benzyl-[2-(4-nitrophenyl)ethyl]amino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one

HRID 1055339노트

반응식

HRID 1055339 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11]OS(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:25]([NH:32][CH2:33][C@@H:34]([C:43]1[CH:52]=[CH:51][C:50]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[C:49]2[C:44]=1[CH:45]=[CH:46][C:47](=[O:61])[NH:48]2)[O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)C(C)C)(C)C.CCOC(C)=O>C(#N)C>[CH2:25]([N:32]([CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH2:33][C@@H:34]([C:43]1[CH:52]=[CH:51][C:50]([O:53][CH2:54][C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)=[C:49]2[C:44]=1[CH:45]=[CH:46][C:47](=[O:61])[NH:48]2)[O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 666727545-[(R)-2-benzylamino 1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-oneHCID 858188714-Nitrobenzenesulfonic Acid 2-(4-Nitrophenyl)ethyl Ester

생성물 1

HCID 667718165-[(R)-2-{Benzyl-[2-(4-nitrophenyl)ethyl]amino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one수율 50.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A stirred solution of 4-nitrobenzenesulfonic acid 2-(4-nitrophenyl)ethyl ester (3.78 g, 10.7 mmol); 5-[(R)-2-benzylamino-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one (4.620 g, 8.975 mmol) and N,N-diisopropylethylamine (3.59 mL, 20.6 mmol) in acetonitrile (39.2 mL) was heated at 65° C. overnight. After cooling the reaction mixture to room temperature, EtOAc (20 mL) was added and this mixture was washed with brine (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound (3.0 g, 50% yield) as a yellow oil.

후처리

  1. washthis mixture was washed with brine (20 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0-30% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-684a4e9224ef4da2ae9bee916e6661e0
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394275B2

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