Carbonic acid sodium salt (1:2) → (R)-2-morpholino-2-phenylacetic acid

HRID 923398笔记

反应方程式

HRID 923398 反应方程式
[NH2:1][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[O:15]1[CH2:16][CH2:17][N:1]([C@H:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3]([OH:5])=[O:4])[CH2:13][CH2:14]1

参与物

5

反应物 3

HCID 10340Carbonic acid sodium salt (1:2)HCID 215212,2'-二溴二乙醚HCID 70134左旋苯甘氨酸

产物 1

HCID 1090521(R)-2-morpholino-2-phenylacetic acid

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

To (R)-2-amino-2-phenylacetic acid (1.0 g, 6.62 mmol), 1-bromo-2-(2-bromoethoxy)ethane (1.686 g, 0.727 mmol) and sodium carbonate (2.103 g, 19.85 mmol) was added ethanol (40 mL) and the resultant mixture heated at 100° C. for 45 hours. After cooling, the resultant solid was removed by filtration and washed with ethanol. The filtrate was concentrated, and then dissolved in ethanol then a solution of 4N aqueous hydrochloric acid added until the pH of the solution was 3. The resultant solid was removed and discarded. The filtrate was concentrated and purified by reversed phase chromatography (C18), eluting with 10-100% acetonitrile in water (0.1% TFA) to give the title compound. MS (ESI) m/z 222 (MA)+.

后处理

  1. temperatureAfter cooling
  2. customthe resultant solid was removed by filtration
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. dissolutiondissolved in ethanol
  6. additiona solution of 4N aqueous hydrochloric acid added until the pH of the solution
  7. customThe resultant solid was removed
  8. concentrationThe filtrate was concentrated
  9. custompurified by reversed phase chromatography (C18)
  10. washeluting with 10-100% acetonitrile in water (0.1% TFA)

来源与证据

ORD记录
ord-af592f40ecca472c9bb07c6e1b03dfa4
来源数据集
uspto-grants-2016_03
专利号
US09278922B2

反应笔记

加载中…