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HRID1486048

反应详情

EQUATION

反应方程式

HRID 1486048 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：COc1ccc2c(Br)cccc2c1CCl
HCID89922511

未命名化合物

结构：C[C@@H](C(=O)N[C@@H]1C(=O)Nc2ccccc2N(C(=O)CS(C)(=O)=O)[C@H]1C)N(C)C(=O)OC(C)(C)C
HCID90082560

未命名化合物

PRODUCTS

生成物

1
结构：COc1ccc2c(Br)cccc2c1CN1C(=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)c2ccccc21
HCID118292699

未命名化合物

收率 50%

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 methyl((S)-1-((2S,3S)-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)carbamate (46 mg, 92.6 μmol) in DMF (232 μl) was added 5-bromo-1-(chloromethyl)-2-methoxynaphthalene (31.7 mg, 111 μmol), cesium carbonate (39.2 mg, 120 μmol), and sodium iodide (18.1 mg, 120 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-((3S,4S)-1-((5-bromo-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 (34.2 mg, 50%) as a white solid. MS m/z 767/769 (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