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Methanesulfonyl chloride → {3,4-Dichloro-5-[(cyclopropyl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]phenyl}methyl methanesulfonate

HRID 337568
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HRID 337568 반응식
[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[C:15]([Cl:21])[C:14]=2[Cl:22])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl.CCOCC>[CH3:32][S:33]([O:20][CH2:19][C:17]1[CH:18]=[C:13]([CH2:12][N:4]([CH:1]2[CH2:3][CH2:2]2)[C:5]([O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[O:11])[C:14]([Cl:22])=[C:15]([Cl:21])[CH:16]=1)(=[O:35])=[O:34]
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6

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 668961381,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(hydroxymethyl)phenyl]methyl}carbamate

생성물 1

HCID 86651664{3,4-Dichloro-5-[(cyclopropyl{[(1,1-dimethylethyl)oxy]carbonyl}amino)methyl]phenyl}methyl methanesulfonate

시약·촉매·용매 2

HCID 3283Diethyl Ether용매
HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 1,1-dimethylethyl cyclopropyl{[2,3-dichloro-5-(hydroxymethyl)phenyl]methyl}carbamate (1 eq.) from the previous step in dichloromethane (0.1 M) was added sequentially at 0 Hunig's base (3 eq.) and methanesulfonyl chloride (1.1 eq.). The resulting solution was stirred at 0° C. for 30 min and then at RT for 15 min. The reaction mixture was then diluted with ether and carefully quenched with 1 N aq. HCl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo to afford the crude title compound as a colorless oil.

후처리

  1. waitat RT for 15 min
  2. customcarefully quenched with 1 N aq. HCl
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo

출처 및 근거

ORD 기록
ord-d7101ec58c7d4660b1084fe09efc01e5
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889714B2

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