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Cesium carbonate → (3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide

HRID 736787
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HRID 736787 반응식
[C:1]([O:5][NH:6][C:7]([C@:9]1([CH3:26])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:34][C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:38]=[C:37]([CH3:45])[CH:36]=1>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][NH:6][C:7]([C@:9]1([CH3:26])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:34][C:35]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[N:38]=[C:37]([CH3:45])[CH:36]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][O:11][CH2:10]1)=[O:8])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 115357194-(Chloromethyl)-2-methylquinolineHCID 86607887(3R,4R)-N-tert-butoxy-4-(4-hydroxyphenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxamide

생성물 1

HCID 86607888(3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide수율 56%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

The crude (3R,4R)-N-tert-butoxy-4-(4-hydroxyphenylsulfonamido)-3-methyl-tetrahydro-2H-pyran-3-carboxamide (1.76 mmol) from Step 9 was dissolved in DMF (20 mL) and cesium carbonate (2.9 g, 8.80 mmol, 5.0 eq) and 4-chloromethyl-2-methylquinoline (602 mg, 2.64 mmol, 1.5 eq) were added. The mixture was stirred at room temperature overnight and then diluted with ethyl acetate (200 mL) and washed with water (100 mL×3). The aqueous layer was re-extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica eluting with 75% ethyl acetate/hexane to yield 0.53 g (56% for three steps) of (3R,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)-tetrahydro-2H-pyran-3-carboxamide as white solid. MS: (M+H)+=542.0

후처리

  1. washwashed with water (100 mL×3)
  2. extractionThe aqueous layer was re-extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica eluting with 75% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-ebdfb3fa18d0467eab5eca3c7e828e05
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07595327B2

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