Glycine → N-环戊氧羰基-L-叔亮氨酸

HRID 2425288笔记

反应方程式

HRID 2425288 反应方程式
[C:1](NCC(O)=O)([CH3:4])([CH3:3])[CH3:2].[C:10](=[O:25])(ON1C(=O)CCC1=O)[O:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[NH2:26][CH2:27][C:28]([OH:30])=[O:29]>C(=O)(O)[O-].[Na+].CC(C)=O>[CH:12]1([O:11][C:10]([NH:26][C@@H:27]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:28]([OH:30])=[O:29])=[O:25])[CH2:13][CH2:14][CH2:15][CH2:16]1

参与物

6

反应物 3

HCID 750GlycineHCID 414246N-T-丁基甘氨酸 钠盐HCID 15927743环戊基-N-琥珀酰亚胺基碳酸酯

产物 1

HCID 23595129N-环戊氧羰基-L-叔亮氨酸

试剂、催化剂与溶剂 2

HCID 180丙酮溶剂HCID 516892碳酸氢钠溶剂

实验过程

In a 5 L RB flask dissolved t-butyl glycine (74 g, 0.56 mol, 1.02 eq.) in saturated sodium bicarbonate (11 vol). Cyclopentyl 2,5-dioxopyrrolidin-1-yl carbonate (126 g, 0.55 mol, 1 eq.) was dissolved in acetone (5.5 vol) and the solution slowly added via addition funnel at room temperature to the solution of the glycine. The reaction mixture was stirred at room temperature until complete (approximately 4 hours). The acetone was removed under reduced pressure and the remaining aqueous solution was extracted with 30% ethyl acetate in hexanes (thrice, 5.5 vol each). The organic layers were discarded. The pH of the aqueous layer was adjusted to 2 with 2 N HCl and then extracted with ethyl acetate (thrice, 5.5 vol). The combined organic layers were dried (Na2SO4), filtered, and the solvent removed under reduced pressure to provide a clear oil the slowly crystallized. The crude product was crystallized from hexanes/ethyl acetate to provide (S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoic acid as a white solid (82 g). The mother liquid was stripped and a second crop of crystals obtained (combined yield 105.54 g).

后处理

  1. customThe acetone was removed under reduced pressure
  2. extractionthe remaining aqueous solution was extracted with 30% ethyl acetate in hexanes (thrice, 5.5 vol each)
  3. extractionextracted with ethyl acetate (thrice, 5.5 vol)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customto provide a clear oil the
  8. customslowly crystallized
  9. customThe crude product was crystallized from hexanes/ethyl acetate

来源与证据

ORD记录
ord-f3ed3b8af1f447648ad9aa013a0138b5
来源数据集
uspto-grants-2011_06
专利号
US07964624B1

反应笔记

加载中…