1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl 3-(3-(2-tert-butylphenoxy)azetidin-1-yl)-3-oxopropanoate

HRID 2041979노트

반응식

HRID 2041979 반응식
[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:16]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][C:18](O)=[O:19].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:18](=[O:19])[CH2:17][C:16]([O:22][CH2:23][CH3:24])=[O:21])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70615Monoethyl malonateHCID 757711-HydroxybenzotriazoleHCID 534095303-(2-Tert-butylphenoxy)azetidine

생성물 1

HCID 59577290Ethyl 3-(3-(2-tert-butylphenoxy)azetidin-1-yl)-3-oxopropanoate수율 53.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 3-(2-tert-butylphenoxy)azetidine (0.35 g, 1.70 mmol), ethyl hydrogen malonate (0.25 g, 1.87 mmol) in methylene chloride (20.0 mL) was added EDCI (0.36 g, 1.87 mmol) and HOBt (0.25 g, 1.87 mmol) at room temperature. After 16 h the reaction mixture was concentrated under reduced pressure, the resulting residue was partitioned between ethyl acetate and water and separated. The organic layer was washed with 10% sodium bicarbonate, saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 50:50 heptane/ethyl acetate) to provide ethyl 3-(3-(2-tert-butylphenoxy)azetidin-1-yl)-3-oxopropanoate (0.29 g, 53%) as a colorless oil.

후처리

  1. concentrationAfter 16 h the reaction mixture was concentrated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate and water
  3. customseparated
  4. washThe organic layer was washed with 10% sodium bicarbonate, saturated sodium chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography (silica gel, 50:50 heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-cd9a9ee655f340bd933c08af08c31938
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586571B2

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