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HRID879180

反应详情

EQUATION

反应方程式

HRID 879180 的结构方程式

REACTANTS

反应物

2
结构：CC([O-])=S.[K+]
HCID23670855

未命名化合物

结构：C[C@H]1C[C@@H](c2ccncc2NC(=O)OC(C)(C)C)C[C@@H](NC(=O)OC(C)(C)C)[C@@H]1OS(C)(=O)=O
HCID86705223

未命名化合物

PRODUCTS

生成物

1
结构：CC(=O)S[C@H]1[C@@H](C)C[C@@H](c2ccncc2NC(=O)OC(C)(C)C)C[C@H]1NC(=O)OC(C)(C)C
HCID86705224

未命名化合物

收率 87%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CN(C)C=O
溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度
60 °C

PROCEDURE

实验过程

To a solution of (+/−)-(1R,2R,4R,6S)-2-(tert-butoxycarbonylamino)-4-(3-(tert-butoxycarbonylamino)pyridin-4-yl)-6-methylcyclohexyl methanesulfonate (1.0 equiv.) in DMF (0.25 M) was added potassium thioacetate (6.0 equiv.). The mixture was stirred for 6 hours in a 60° C. bath under Ar. Upon cooling and the residue was partitioned between EtOAc and H2O. The organic layer was washed with H2O (3×), Na2CO3(sat.), NaCl(sat.), dried over MgSO4, filtered, concentrated and purified by ISCO SiO2 chromatography to yield (+/−)S-((1S,2R,4R,6S)-2-((tert-butoxycarbonyl)amino)-4-(3-((tert-butoxycarbonyl)amino)pyridin-4-yl)-6-methylcyclohexyl) ethanethioate in 87% yield. LC/MS (m/z)=480.3 (MH+), Rt=0.82 min.

WORKUP

后处理

  1. temperatureUpon cooling
  2. customthe residue was partitioned between EtOAc and H2O
  3. washThe organic layer was washed with H2O (3×), Na2CO3(sat.), NaCl(sat.)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by ISCO SiO2 chromatography