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HRID1486061

反应详情

EQUATION

反应方程式

HRID 1486061 的结构方程式

REACTANTS

反应物

4
结构：[I-].[Na+]
HCID5238

Sodium Iodide

INa

结构：O=C([O-])[O-].[Cs+].[Cs+]
HCID10796

Cesium carbonate

CCs2O3

结构：CS(=O)(=O)OCc1c(C2CC2)cnc2ccccc12
HCID89922492

未命名化合物

结构：CC(=O)N1c2ccccc2NC(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)[C@@H]1C
HCID118292585

未命名化合物

PRODUCTS

生成物

1
结构：CC(=O)N1c2ccccc2N(Cc2c(C3CC3)cnc3ccccc23)C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)[C@@H]1C
HCID118292641

未命名化合物

收率 45.3%

AUXILIARIES

试剂、催化剂与溶剂

2
结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

结构：CCOC(C)=O
溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

To a rt solution of tert-butyl(S)-1-((2S,3S)-1-acetyl-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (100 mg, 239 μmol) in DMF (597 μl) was added (3-cyclopropylquinolin-4-yl)methyl methanesulfonate (79.5 mg, 287 μmol), cesium carbonate (101 mg, 311 μmol), and sodium iodide (46.6 mg, 311 μmol). The reaction was stirred at rt for 16 h, then diluted with EtOAc, washed with H2O and sat. aq. NaCl, dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash chromatography to provide tert-butyl(S)-1-((2S,3S)-1-acetyl-5-((3-cyclopropylquinolin-4-yl)methyl)-2-methyl-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (65 mg, 45%) as a white solid. MS m/z 600 (MH)+.

WORKUP

后处理

  1. washwashed with H2O and sat. aq. NaCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography