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HRID1437820

反应详情

EQUATION

反应方程式

HRID 1437820 的结构方程式

REACTANTS

反应物

2
结构：[C-]#N.[Na+]
HCID8929

Sodium cyanide (Na(CN))

CNNa

结构：COC(=O)[C@H]1O[C@@H](Oc2ccc([C@@H]3[C@@H](CC[C@H](OC(C)=O)c4ccc(F)cc4)C(=O)N3c3ccc(C#CC(=O)O)cc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O
HCID86601877

未命名化合物

PRODUCTS

生成物

1
结构：O=C(O)C#Cc1ccc(N2C(=O)[C@H](CC[C@H](O)c3ccc(F)cc3)[C@H]2c2ccc(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)cc2)cc1
HCID67055604

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CO
溶剂HCID887

Methanol

CH4O

PROCEDURE

实验过程

A solution of 4-{(2S,3R)-3-[(3S)-3-(acetyloxy)-3-(4-fluorophenyl)propyl]-1-[4-(carboxyethynyl)phenyl]-4-oxoazetidin-2-yl}phenyl methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosiduronate (10d) and sodium cyanide (˜1 mg, 0.020 mmol) in methanol (3 mL) was heated to 45° C. After 22 h, the reaction mixture was concentrated under reduced pressure and dissolved in methanol/water/triethylamine (1:7:2, 1 mL). After stirring at room temperature for approximately 1 h, the volatiles were evaporated in vacuo and the crude residue purified by preparative reversed phase high performance liquid chromatography on YMC Pack Pro C18 phase (gradient elution; 10-60% acetonitrile/water as eluent, 0.1% TFA modifier) to give the title compound (10e), m/z (ES) 442.0 (M-sugar-OH)+, 618.0 (M−OH)+; HRMS (ES) m/z calcd. for C33H31FNO11 (MH+) 636.1881, found 636.1889

WORKUP

后处理

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in methanol/water/triethylamine (1:7:2, 1 mL)
  3. customthe volatiles were evaporated in vacuo
  4. customthe crude residue purified by preparative reversed phase high performance liquid chromatography on YMC Pack Pro C18 phase (gradient elution; 10-60% acetonitrile/water as eluent, 0.1% TFA modifier)