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Thionyl Chloride → Tert-butyl 3-[3-(1-chloroethyl)-6-cyano-2-methoxy-5-methylphenyl]azetidine-1-carboxylate

HRID 1499912
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HRID 1499912 반응식
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([CH:10](O)[CH3:11])=[C:5]([O:13][CH3:14])[C:4]=1[CH:15]1[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]1)#[N:2].S(Cl)([Cl:28])=O>C(Cl)Cl.CN(C)C=O>[Cl:28][CH:10]([C:6]1[C:5]([O:13][CH3:14])=[C:4]([CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[C:3]([C:1]#[N:2])=[C:8]([CH3:9])[CH:7]=1)[CH3:11]
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참가 물질

5

반응물 2

HCID 24386Thionyl ChlorideHCID 86677832Tert-butyl 3-[2-cyano-5-(1-hydroxyethyl)-6-methoxy-3-methylphenyl]azetidine-1-carboxylate

생성물 1

HCID 86677833Tert-butyl 3-[3-(1-chloroethyl)-6-cyano-2-methoxy-5-methylphenyl]azetidine-1-carboxylate수율 100%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane
용매

실험 절차

The tert-butyl 3-[2-cyano-5-(1-hydroxyethyl)-6-methoxy-3-methylphenyl]azetidine-1-carboxylate (2.1 g, 6.4 mmol) was taken up in methylene chloride (50.0 mL) and N,N-dimethylformamide (0.59 mL), cooled in an ice bath and the thionyl chloride (0.56 mL, 7.7 mmol) was added slowly. After stirring for 2 hrs the reaction was complete by LC/MS and was partitioned between ethyl acetate and water. The combined organic layer was washed with water saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to give crude tert-butyl 3-[3-(1-chloroethyl)-6-cyano-2-methoxy-5-methylphenyl]azetidine-1-carboxylate as an oil (2.2 g, 100%). LCMS calculated for C15H18ClN2O3(M+H)+: m/z=309.1; found: 309.1.

후처리

  1. customwas partitioned between ethyl acetate and water
  2. washThe combined organic layer was washed with water saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8d74fc8a502a4c62a9113a4960bb3306
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199982B2

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