Acetyl chloride → (S)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)-2-hydroxypropyl acetate

HRID 705319노트

반응식

HRID 705319 반응식
[Cl:1][CH2:2][C@@H:3]([OH:27])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:15]2[CH:26]=[CH:25][C:18]([O:19][CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])=[CH:17][CH:16]=2)([CH3:14])[CH3:13])=[CH:8][CH:7]=1.N1C(C)=CC=CC=1C.[C:36](Cl)(=[O:38])[CH3:37]>ClCCl>[C:36]([O:23][CH2:22][C@@H:21]([OH:24])[CH2:20][O:19][C:18]1[CH:17]=[CH:16][C:15]([C:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][C@H:3]([OH:27])[CH2:2][Cl:1])=[CH:11][CH:10]=2)([CH3:14])[CH3:13])=[CH:26][CH:25]=1)(=[O:38])[CH3:37]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 79372,6-LutidineHCID 45107537Ralaniten

생성물 1

HCID 86292878(S)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)-2-hydroxypropyl acetate수율 34%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (R)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol (1000 mg, 2.53 mmol) in anhydrous dichloromethane (8.0 mL) at −78° C. were successively added 2,6-lutidine (590 μL, 5.06 mmol) and acetic chloride (144 μL, 2.02 mmol) dropwise. After 1 h, the reaction mixture was quenched with an aqueous solution of sodium chloride and stirred for 15 min, and the resulting mixture was extracted twice with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate and filtered. Solvents were evaporated, and the resulting crude material was purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane) to provide the title compound (300 mg, 27%) as a sticky solid.

후처리

  1. customat −78° C.
  2. customthe reaction mixture was quenched with an aqueous solution of sodium chloride
  3. extractionthe resulting mixture was extracted twice with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customSolvents were evaporated
  7. customthe resulting crude material was purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-2c119ae4179649c99a9bb0e920fe3751
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173939B2

반응 노트

불러오는 중…