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Sodium Bicarbonate → [(3R,4R,7R)-3-Hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-yl]-carbamic acid tert-butyl ester

HRID 1790657
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HRID 1790657 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7](Cl)(=[O:9])=[O:8].[C:11]([O:15][C:16](=[O:27])[NH:17][C@@H:18]1[CH2:24][CH2:23][C@@H:22]([CH3:25])[NH:21][CH2:20][C@H:19]1[OH:26])([CH3:14])([CH3:13])[CH3:12].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CCOC(C)=O>[C:11]([O:15][C:16](=[O:27])[NH:17][C@@H:18]1[CH2:24][CH2:23][C@@H:22]([CH3:25])[N:21]([S:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)(=[O:9])=[O:8])[CH2:20][C@H:19]1[OH:26])([CH3:13])([CH3:12])[CH3:14]
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참가 물질

7

반응물 3

HCID 516892Sodium BicarbonateHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 68998497((3R,4R,7R)-3-Hydroxy-7-methyl-azepan-4-yl)-carbamic acid tert-butyl ester

생성물 1

HCID 69000299[(3R,4R,7R)-3-Hydroxy-7-methyl-1-(pyridine-2-sulfonyl)-azepan-4-yl]-carbamic acid tert-butyl ester수율 65.6%

시약·촉매·용매 3

HCID 962Water
용매
HCID 6344Dichloromethane용매
HCID 8857Ethyl Acetate용매

실험 절차

Pyridine-2-sulfonyl chloride (0.55 g, 3.1 mmol) was added to a solution ((3R,4R,7R)-3-Hydroxy-7-methyl-azepan-4-yl)-carbamic acid tert-butyl ester (0.58 g, 0.2.4 mmol), sodium bicarbonate (0.84 g, 10 mmol) in CH2Cl2 (10 ml) and H2O (3 ml) and was stirred at RT for 30 minutes. The reaction mixture was diluted with EtOAc (100 ml), washed with H2O, brine, dried with magnesium sulfate, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 45:55 EtOAC/hexanes) to yield the title compound (0.6 g, 65%): Electrospray mass spec: M+H+=386.27.

후처리

  1. washwashed with H2O, brine
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo by rotary evaporation
  5. customchromatographed (silica gel, 45:55 EtOAC/hexanes)

출처 및 근거

ORD 기록
ord-7eabce3c0fd649deb1c2ee99f6f93d3e
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07071184B2

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