Hydrochloric Acid → Leucyl-phenylalanine amide

HRID 1768869노트

반응식

HRID 1768869 반응식
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH2:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl>C(OCC)(=O)C>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH2:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 7385739tert-butyl N-[(2S)-1-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate

생성물 1

HCID 3082491Leucyl-phenylalanine amide수율 74%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

De-(1,1-dimethylethoxy)carbonylation of Boc-Leu-Phe-NH2 (24.0 g.) was carried out using hydrogen chloride in ethyl acetate (4.4N, 200 ml.) for 2 hr. at room temperature. Upon attempted extraction with ethyl acetate the product unexpectedly entered the saturated aqueous sodium bicarbonate wash solution, which was subjected in its entirety to reverse phase HPLC on octadecylsilated silica gel. The column was washed with water. The product was eluted with methanol and crystallized from ethanol-ether-hexane affording H-Leu-Phe-NH2 as a tan solid (13.0 g., 74% yield, m.r. 127°-131° C.).

후처리

  1. customfor 2 hr
  2. customat room temperature
  3. extractionextraction with ethyl acetate the product
  4. washwash solution, which
  5. washThe column was washed with water
  6. washThe product was eluted with methanol
  7. customcrystallized from ethanol-ether-hexane

출처 및 근거

ORD 기록
ord-98a9155ea31a457a98cd3c88e1ce2607
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05378803

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