Triethylamine → 3-(3-(4-(Tert-butyl)phenyl)ureido)propyl methanesulfonate

HRID 1024660노트

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HRID 1024660 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([NH:14][CH2:15][CH2:16][CH2:17][OH:18])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].CC(=O)OCC>C(Cl)Cl>[CH3:26][S:27]([O:18][CH2:17][CH2:16][CH2:15][NH:14][C:12]([NH:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=1)=[O:13])(=[O:29])=[O:28]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 535206861-(4-Tert-butylphenyl)-3-(3-hydroxypropyl)urea

생성물 1

HCID 867023653-(3-(4-(Tert-butyl)phenyl)ureido)propyl methanesulfonate수율 108.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

A solution of 1-(4-tert-butylphenyl)-3-(3-hydroxypropyl)urea (563 mg, 2.25 mmol) in methylene chloride (14 mL) was cooled at 0° C. and treated dropwise with triethylamine (0.376 mL, 2.70 mmol) followed by methanesulfonyl chloride (0.191 mL, 2.47 mmol) and the mixture was stirred at 0° C. until complete by TLC. After 30 minutes, the reaction was complete by TLC (100% EA). The reaction mixture was diluted with 15 mL CH2Cl2 and the organic phase was washed with 15 mL portions of 1N HCl, sat NaHCO3 and H2O and dried over MgSO4. The solution was filtered and concentrated to a viscous oil that was placed under high vacuum to yield the title compound (800 mg) as a colorless viscous oil that was stored in the freezer: MS (ESI+) for C15H24N2O4S m/z 329.1 (M+H)+; HPLC purity 93% (ret. time, 3.95 min).

후처리

  1. washthe organic phase was washed with 15 mL portions of 1N HCl
  2. dry with materialdried over MgSO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated to a viscous oil that

출처 및 근거

ORD 기록
ord-c118bc71cc754cbbbe3a48e5ddbbe66d
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722877B2

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