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Triethylamine → trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-yl methanesulfonate

HRID 1425383
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HRID 1425383 반응식
C(N(CC)CC)C.[C:8]1([CH:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]2[CH2:18][C@@H:17]([OH:19])[C@@H:16]2[CH2:20][CH3:21])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl.C(OCC)(=O)C>[CH3:28][S:29]([O:19][C@@H:17]1[CH2:18][N:15]([CH:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:16]1[CH2:20][CH3:21])(=[O:31])=[O:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86648812trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-ol

생성물 1

HCID 86648814trans(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-yl methanesulfonate수율 90.9%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회
HCID 8857
Ethyl Acetate
용매

실험 절차

Triethylamine (0.94 mL, 6.74 mmol) was added to a solution of trans(±)-1-(Diphenylmethyl)-2-ethylazetidin-3-ol obtained in Example (234b) (1.20 g, 4.49 mmol) in dichloromethane (8 mL). Then, a solution of methanesulfonyl chloride (0.45 mL, 5.83 mmol) in dichloromethane (1.5 mL) was added dropwise at room temperature, followed by stirring for four hours. The reaction solution was diluted with ethyl acetate, washed with water and brine, and then dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1) to obtain 1.41 g of the title compound as a pale yellow oily substance (91%).

후처리

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-cc578f873d52450a8f3a9610a5a267d0
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927588B2

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