聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → Z-Phe-Gly-Leu-OH

HRID 236457

反应方程式

HRID 236457 反应方程式
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:23][CH2:24][C:25]([NH:27][C@H:28]([C:33]([OH:35])=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31])=[O:26].C(N(CC)CC)C.O>O1CCOCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:23][CH2:24][C:25]([NH:27][C@H:28]([C:33]([OH:35])=[O:34])[CH2:29][CH:30]([CH3:32])[CH3:31])=[O:26])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 8471三乙胺HCID 70878N-苄氧羰基-L-苯丙氨酸HCID 92843甘氨酰-L-亮氨酸

产物 1

HCID 131715018Z-Phe-Gly-Leu-OH收率 73.6%

试剂、催化剂与溶剂 1

HCID 312751,4-二氧六环溶剂

实验过程

The N-hydroxysuccinimide ester of Z-Phe-OH (19.15 g, 48.3 mmol) was dissolved in 50 mL of dioxane and the resulting solution was filtered into a solution consisting of H-Gly-Leu-OH (10.0 g, 53.1 mmol), triethylamine (10.1 mL, 72.4 mmol), and water (50 mL). This reaction mixture was stirred overnight at about 23°, and then concentrated approximately 60% by evaporation. The resulting concentrated solution was diluted with 1.0N hydrochloric acid until acidic. Product Z-Phe-Gly-Leu-OH was extracted into ethyl acetate, and the resulting extract was washed with 0.2N hydrochloric acid, followed by saturated aqueous sodium chloride adjusted to 0.10N hydrochloric acid. After washing, the ethyl acetate solution was dried over anhydrous sodium sulfate and filtered. The ethyl acetate was then evaporated to yield 22.5 g of a white, foamy product, which was subsequently crystallized from ethyl acetate to yield 16.7 g of Z-Phe-Gly-Leu-OH (m.p. 147°-148°).

后处理

  1. filtrationthe resulting solution was filtered into a solution
  2. concentrationconcentrated approximately 60%
  3. customby evaporation
  4. additionThe resulting concentrated solution was diluted with 1.0N hydrochloric acid until acidic
  5. extractionProduct Z-Phe-Gly-Leu-OH was extracted into ethyl acetate
  6. extractionthe resulting extract
  7. washwas washed with 0.2N hydrochloric acid
  8. washAfter washing
  9. dry with materialthe ethyl acetate solution was dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customThe ethyl acetate was then evaporated
  12. customto yield 22.5 g of a white, foamy product, which
  13. customwas subsequently crystallized from ethyl acetate

来源与证据

ORD记录
ord-a0521274689e4da7b3dba97f0b6cf983
来源数据集
uspto-grants-1987_02
专利号
US04644055

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