N-甲基吗啉 → HCID 178450981，化合物

HRID 36804

反应方程式

HRID 36804 反应方程式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][CH:14]([CH3:16])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[CH2:36]([O:40][CH:41]([O:51][CH2:52][CH2:53][CH2:54][CH3:55])[C@H:42]([CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:50])[NH2:49])[NH2:43])[CH2:37][CH2:38][CH3:39]>CN(C)C=O.C(N(CC)CC)C>[CH2:52]([O:51][CH:41]([O:40][CH2:36][CH2:37][CH2:38][CH3:39])[C@H:42]([CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:49])[NH2:50])[NH:43][C:17](=[O:19])[C@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:53][CH2:54][CH3:55]

参与物

7

反应物 4

HCID 7972N-甲基吗啉HCID 62365氯甲酸异丁酯HCID 74840N-苄氧羰基-L-亮氨酸HCID 178450993HCID 178450993，化合物

产物 1

HCID 178450981HCID 178450981，化合物收率 69.7%

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺溶剂2 次HCID 8471三乙胺溶剂

反应条件

温度
-15 °C

实验过程

In 25 ml of dimethylformamide was dissolved 2.65 g of N-benzyloxycarbonyl-L-leucine. After cooling to -15° C., 1.10 ml of N-methylmorpholine and then 1.37 ml of isobutyl chloroformate were added to the solution while stirring the solution at the same temperature. The mixture was sitrred at -15° C. for 5 minutes. On the other hand, 3.25 g of L-argininal dibutyl acetal hydrochloride (Example 2) was dissolved in 30 ml of dimethylformamide and 1.40 ml of triethylamine was added to the solution. The resulting solution was dropwise added at -10° C. to the mixed acid anhydride suspension which had been previously prepared. Stirring was continued at the same temperature for an hour and then at 0° C. for an hour. The resulting reaction solution was concentrated under reduced pressure and the residue was dissolved in 100 ml of chloroform. The solution was washed successively with 10% citric acid aqueous solution (30 ml×2), saturated sodium chloride aqueous solution (30 ml×1), saturated sodium hydrogencarbonate aqueous solution (30 ml×2) and saturated sodium chloride aqueous solution (30 ml×2). After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was subjected to column chromatography using silica gel as a carrier and developed with chloroform: methanol=20:1 (v/v). The fraction showing Rf: 0.48 (under the same conditions as in Example 1 (A) 4) which was positive in the Sakaguchi reaction, was concentrated under reduced pressure to give 3.73 g of N-benzyloxycarbonyl-L-leucyl-L-argininal dibutyl acetal.

后处理

  1. customhad been previously prepared
  2. stirringStirring
  3. waitwas continued at the same temperature for an hour
  4. waitat 0° C. for an hour
  5. customThe resulting reaction solution
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in 100 ml of chloroform
  8. washThe solution was washed successively with 10% citric acid aqueous solution (30 ml×2), saturated sodium chloride aqueous solution (30 ml×1), saturated sodium hydrogencarbonate aqueous solution (30 ml×2) and saturated sodium chloride aqueous solution (30 ml×2)
  9. dry with materialAfter drying over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customwas positive in the Sakaguchi reaction
  12. concentrationwas concentrated under reduced pressure

来源与证据

ORD记录
ord-6b218140444744549e981b24dba79eb8
来源数据集
uspto-grants-1995_05
专利号
US05416238

关联笔记

加载中…