Water → Z-Phe-Gly-Leu-OH

HRID 236457

반응식

HRID 236457 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 92843Glycyl-L-leucine

생성물 1

HCID 131715018Z-Phe-Gly-Leu-OH수율 73.6%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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°).

후처리

  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

출처 및 근거

ORD 기록
ord-a0521274689e4da7b3dba97f0b6cf983
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04644055

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