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

HRID 524411ノート

反応式

HRID 524411 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-53e03ceedca14f0591086f255a1d91fa
出典データセット
uspto-grants-2016_05
特許番号
US09340506B2

反応ノート

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