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HRID1486095

反应详情

EQUATION

反应方程式

HRID 1486095 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：COc1ccc2ccccc2c1CCl
HCID13356646

1-(Chloromethyl)-2-methoxynaphthalene

C12H11ClO

结构：C[C@@H](C(=O)N[C@@H]1C(=O)Nc2ccc(C#N)cc2N(C(=O)CS(C)(=O)=O)[C@H]1C)N(C)C(=O)OC(C)(C)C
HCID72713840

未命名化合物

PRODUCTS

生成物

1
结构：COc1ccc2ccccc2c1CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)[C@H](C)N(C(=O)CS(C)(=O)=O)c2cc(C#N)ccc21
HCID72712778

未命名化合物

收率 38.4%

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)-8-cyano-2-methyl-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (108 mg, 207 μmol) in DMF (518 μl) was added 1-(chloromethyl)-2-methoxynaphthalene (47.1 mg, 228 μmol), cesium carbonate (81.0 mg, 248 μmol), and sodium iodide (37.2 mg, 248 μmol). The reaction was stirred at rt for 1.5 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 then reverse phase preparative HPLC to provide tert-butyl(S)-1-((3S,4S)-7-cyano-1-((2-methoxynaphthalen-1-yl)methyl)-4-methyl-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (55 mg, 38%) as a white solid. MS m/z 714 (MNa)+.

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