N,N-二异丙基乙胺 → Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-isopropyl-1,3-thiazole-5-carboxylate

HRID 43882

反应方程式

HRID 43882 反应方程式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:14]1[S:15][C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:17]([CH:19]([CH3:21])[CH3:20])[N:18]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][N:11]([C:14]2[S:15][C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:17]([CH:19]([CH3:20])[CH3:21])[N:18]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参与物

6

反应物 3

HCID 81531N,N-二异丙基乙胺HCID 15194053-N-叔丁氧羰基胺基环丁胺HCID 9943530Ethyl 2-bromo-4-isopropylthiazole-5-carboxylate

产物 1

HCID 67548483Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-isopropyl-1,3-thiazole-5-carboxylate收率 66%

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺溶剂HCID 8857乙酸乙酯溶剂

实验过程

A solution of 3-tert-butoxycarbonylaminoazetidine (136 mg, 0.79 mmol), ethyl 2-bromo-4-isopropyl-1,3-thiazole-5-carboxylate obtained in Example (23b) (200 mg, 0.72 mmol) and diisopropylethylamine (0.25 mL, 1.44 mmol) in DMF (8 mL) was stirred at 90° C. for 11 hours. The reaction solution was diluted with ethyl acetate, and then the mixture was washed with 10% saline and dried over anhydrous magnesium sulfate. Following filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1) to obtain 175 mg of the title compound as a white solid (66%).

后处理

  1. washthe mixture was washed with 10% saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1)

来源与证据

ORD记录
ord-99c2381ecc4b4614b08aeb3b6ae8d7af
来源数据集
uspto-grants-2013_09
专利号
US08536197B2

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