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Water → Tert-butyl [4-(6-methoxy-quinolin-4-yloxymethyl)-cyclohexyl]carbamate

HRID 1354228
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HRID 1354228 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[OH:15].[C:16]([O:20][C:21]([NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30]OS(C)(=O)=O)[CH2:26][CH2:25]1)=[O:22])([CH3:19])([CH3:18])[CH3:17].O>CN(C=O)C.C(OCC)(=O)C>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[C:8]2[O:15][CH2:30][CH:27]1[CH2:26][CH2:25][CH:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:29][CH2:28]1
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참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 178453973HCID 178453973, 화합물HCID 178487890HCID 178487890, 화합물

생성물 1

HCID 58603138Tert-butyl [4-(6-methoxy-quinolin-4-yloxymethyl)-cyclohexyl]carbamate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

실험 절차

NaH dispersion (55% in mineral oil, 88 mg, 2 mmol) was added to a suspension of 6-methoxy-4-hydroxyquinoline (350 mg, 2 mmol) in DMF (4 ml) and stirred at room temperature until a solution formed. trans-Methanesulphonic acid 4-tert-butoxycarbonylaminocyclohexylmethyl ester (635 mg, 2 mmol) was added and the reaction mixture was stirred overnight at 80° C. Water was added to the mixture and extraction was carried out with ethyl acetate. Organic extracts washed with water, dried over Na2SO4 and concentrated. The crude product was purified by chromatography on silica gel (DCM/MeOH 9:1).

후처리

  1. customformed
  2. stirringthe reaction mixture was stirred overnight at 80° C
  3. washOrganic extracts washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by chromatography on silica gel (DCM/MeOH 9:1)

출처 및 근거

ORD 기록
ord-4e4ad4bcad434403aae8e92531f49556
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07223776B2

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