Water → Ammonium Hydroxide

HRID 1858108노트

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HRID 1858108 반응식
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([CH2:27]C=C)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])(C)(C)C.[O:40]1[CH2:44][CH2:43]CC1.O.C[N+]1([O-])CC[O:50]CC1.[C:54]([OH:58])([CH3:57])([CH3:56])[CH3:55]>[Os](=O)(=O)(=O)=O>[OH-:5].[NH4+:8].[C:54]([O:58][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([CH2:27][CH:44]([OH:40])[CH2:43][OH:50])[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=1)=[O:7])([CH3:57])([CH3:56])[CH3:55]

참가 물질

8

반응물 5

HCID 962WaterHCID 6386tert-ButanolHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 538248342-{2-[6-Allyl-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

생성물 2

HCID 14923Ammonium Hydroxide수율 10%HCID 540195562-{2-[7-Chloro-6-(2,3-dihydroxypropyl)-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 30318Osmium Tetroxide촉매

실험 절차

To a solution of 2-{2-[6-allyl-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (EXAMPLE 4.1 Step E, 6.0 g in a mixture of 80 mL tert-butanol, 24 mL tetrahydrofuran and 8 mL water) was added 1.4 g 4-methylmorpholine N-oxide followed by 140 mg osmium tetraoxide and the mixture stirred at room temperature. After 20 hours, the mixture was concentrated in vacuo and the residue dissolved in ethyl acetate and washed sequentially with water and brine. The combined organics were dried over sodium sulfate and purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:1; then methylene chloride:10% ammonium hydroxide in methanol, 9:1) to give the title compound (5.7 g).

후처리

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. custompurified by flash chromatography on silica gel (ethyl acetate

출처 및 근거

ORD 기록
ord-b9c281a315e94c9d910aa18f430d9851
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150352

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