甲苯 → N-苄氧羰基-L-脯氨酸

HRID 21765

反应方程式

HRID 21765 反应方程式
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Cl[C:10]([O:12]C1C=CC=CC=1)=[O:11].[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>[OH-].[Na+]>[C:10]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])([O:12][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:11]

参与物

5

反应物 3

HCID 1140甲苯HCID 15891氯甲酸苯酯HCID 145742L-脯氨酸

产物 1

HCID 101987N-苄氧羰基-L-脯氨酸收率 98%

试剂、催化剂与溶剂 1

HCID 14798二甲基对苯二胺二盐酸溶剂2 次

反应条件

温度
0 °C

实验过程

L-Proline (10 g, 86.6 mmol) was dissolved in 66 mL of 2N NaOH and cooled to 0° C. To this solution were slowly and simultaneously added 34.35 mL of a solution of phenyl chloroformate in toluene (104.2 mmol) and 33 mL of 4N NaOH, over a period of 1 hr, while maintaining the reaction temperature at 0° C. and the pH above 7. After all reactants were added, the reaction was stirred for 6 hr at room temperature. The solution was then extracted with ether. The remaining aqueous layer was neutralized to pH 6-7 with 1N HCl, then extracted with ethyl acetate. The extract was dried over Na2SO4 and concentrated to afford 21.19 g of the title product (98% yield). 1H NMR (CDCl3) δ 9.55 (d, 1H), 7.3 (s, 5H), 5.25 (d, 2H), 4.35 (t, 1H), 4.20 (t, 1H), 1.8-2.2 (m, 4H).

后处理

  1. temperaturewhile maintaining the reaction temperature at 0° C.
  2. additionAfter all reactants were added
  3. extractionThe solution was then extracted with ether
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over Na2SO4
  6. concentrationconcentrated

来源与证据

ORD记录
ord-c176d87d6c3c4a96ab95c902ab9d98fb
来源数据集
uspto-grants-1995_06
专利号
US05424444

关联笔记

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