Isopropanol → Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate

HRID 524411노트

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HRID 524411 반응식
[C:1]([O:5][C:6]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:9]1[S:10][CH:11]=[C:12]([C:14](=[N+]=[N-])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:31]([OH:34])([CH3:33])[CH3:32]>C(Cl)Cl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[C:1]([O:5][C:6]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:9]1[S:10][CH:11]=[C:12]([CH:14]([O:34][CH:31]([CH3:33])[CH3:32])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

참가 물질

5

반응물 2

HCID 3776IsopropanolHCID 86669544Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-diazo-acetate

생성물 1

HCID 68182441Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate수율 85.8%

시약·촉매·용매 2

HCID 423677Acetic acid, rhodium salt (4:2)촉매HCID 6344Dichloromethane용매2회

실험 절차

Ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-diazo-acetate (0.6 g, 1.38 mmol) was dissolved in DCM (10 mL) under argon atmosphere. To this solution, iso-propanol (0.12 mL, 1.66 mmol) was added followed by rhodium (II) acetate dimer (12 mg, 0.028 mmol). Mixture was stirred at room temperature for 30 min. then diluted with DCM (10 mL). Organic layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a crude product which was purified by silica gel column chromatography using 20% ethyl acetate in hexane to provide ethyl 2-[2-[tert-butoxycarbonyl-[(4-methoxyphenyl)methyl]amino]thiazol-4-yl]-2-isopropoxy-acetate (0.55 g).

후처리

  1. washOrganic layer was washed with water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude product which
  5. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-53e03ceedca14f0591086f255a1d91fa
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340506B2

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