Triacetoxyperiodinane → tert-Butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate

HRID 924391노트

반응식

HRID 924391 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[NH:21][C:22]([C:24]2[C:33]([NH:34][C:35](=[O:44])[O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:32][C:31]3[C:26](=[CH:27][C:28]([CH:45]([OH:47])[CH3:46])=[CH:29][CH:30]=3)[N:25]=2)=[O:23])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:45]([C:28]1[CH:27]=[C:26]2[C:31]([CH:32]=[C:33]([NH:34][C:35]([O:36][CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)=[O:44])[C:24]([C:22]([NH:21][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][C:15]=3[N:11]3[CH2:12][CH2:13][CH2:14][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10]3)=[O:23])=[N:25]2)=[CH:30][CH:29]=1)(=[O:47])[CH3:46]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 86726871Benzyl [2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(1-hydroxyethyl)quinolin-3-yl]carbamate

생성물 1

HCID 86726872tert-Butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate수율 100.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

A solution of benzyl [2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(1-hydroxyethyl)quinolin-3-yl]carbamate (0.100 g, 0.156 mmol) (from Example 15, step 7) in DCM (0.50 mL) was mixed with a solution of Dess-Martin periodinane (0.099 g, 0.23 mmol) in DCM (0.50 mL, 7.8 mmol). The reaction mixture was stirred at room temperature for 18 h. The crude mixture was diluted with DCM and washed with aq. NaOH. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to give the sub-title compound (100 mg, 100%). LCMS calc. for C35H39N6O6 (M+H)+: m/z=639.2. Found: 639.2.

후처리

  1. washwashed with aq. NaOH
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-dd787360a6fc4b639b37c87bb9640404
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278950B2

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