N,N'-二环己基碳二亚胺 → Ethyl N-(1-((benzyloxy)carbonyl)-L-prolyl)-L-leucinate

HRID 1589308

反应方程式

HRID 1589308 反应方程式
[CH2:1]1[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[C@H:3]([C:16]([OH:18])=O)[CH2:2]1.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:44]([O:46][C:47](=[O:54])[C@H:48]([CH2:50][CH:51]([CH3:53])[CH3:52])[NH2:49])[CH3:45]>C(Cl)Cl.C(N(CC)CC)C>[CH2:44]([O:46][C:47](=[O:54])[C@H:48]([CH2:50][CH:51]([CH3:53])[CH3:52])[NH:49][C:16](=[O:18])[C@@H:3]1[CH2:2][CH2:1][CH2:5][N:4]1[C:6]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:7])[CH3:45]

参与物

7

反应物 4

HCID 10868N,N'-二环己基碳二亚胺HCID 757711-羟基苯并三唑(HOBT)HCID 75971L-亮氨酸乙酯HCID 101987N-苄氧羰基-L-脯氨酸

产物 1

HCID 6453075Ethyl N-(1-((benzyloxy)carbonyl)-L-prolyl)-L-leucinate

试剂、催化剂与溶剂 2

HCID 6344二氯甲烷溶剂2 次HCID 8471三乙胺溶剂

实验过程

To a stirred solution of Z-L-proline (12.7 g, 0.051M) in CH2Cl2 (200 ml) cooled to 0° was added 1-hydroxy benzotriazole (7.0 g) followed by a solution of DCC (10.6 g) in CH2Cl2 (50 ml). After 30 min. at 0° L-leucine ethyl ester (10.0 g, 0.051 molM) was added followed by triethylamine (15 ml) and the reaction mixture was then left to stir and warm up to room temperature overnight. The reaction mixture was then filtered and washed in turn with saturated aq. NaHCO3 (250 ml×3), H2O (250 ml), dilute aq. HCl (1 M, 250 ml×3) and water (250 ml×2). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to an oil which subsequently crystallised. Recrystallisation from ethyl acetate/hexane gave N-(benzyloxycarbonyl)-L-prolyl-L-leucine ethyl ester as a white crystalline solid, 15.5 g, (78%); m.p. 67°-68°; (Found: C, 64.55; H, 7.79; N, 7.22. C21H30N2O5 requires C, 64.61; H, 7.74; N, 7.17%); νmax (CHCl3) 1740 and 1680 cm-1 ; δ(CDCl3) 0.7-0.95 (6H, m, CH(CH3)2); 1.18 (3H, m, OCH2CH3); 1.3-1.95 and 2.05-2.25 (7H, m, CH2CH2, CH2CH(CH3)2); 3.4 (2H, m, CH2N); 4.05 (2H, m, OCH2CH3); 4.25 (2H, m, α-CH); 4.98 and 5.05 (together 2H, respectively q, J=7 Hz, and m, CH2C6H5); 7.35 (5H, broad s, C6H5) and 8.26 (1H, m, CONH); m/e 391 (100%, [m+1]+).

后处理

  1. waitthe reaction mixture was then left
  2. filtrationThe reaction mixture was then filtered
  3. washwashed in turn with saturated aq. NaHCO3 (250 ml×3), H2O (250 ml), dilute aq. HCl (1 M, 250 ml×3) and water (250 ml×2)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to an oil which
  7. customsubsequently crystallised
  8. customRecrystallisation from ethyl acetate/hexane

来源与证据

ORD记录
ord-d834726b3f4b4f369343abd3b28c594a
来源数据集
uspto-grants-1986_02
专利号
US04568666

关联笔记

加载中…