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

HRID 2041979ノート

反応式

HRID 2041979 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cd9a9ee655f340bd933c08af08c31938
出典データセット
uspto-grants-2013_11
特許番号
US08586571B2

反応ノート

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