Hydrochloric Acid → Leucyl-phenylalanine amide

HRID 1768869ノート

反応式

HRID 1768869 の反応式
[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]

参加物

4

反応物 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

生成物 1

HCID 3082491Leucyl-phenylalanine amide収率 74%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-98a9155ea31a457a98cd3c88e1ce2607
出典データセット
uspto-grants-1995_01
特許番号
US05378803

反応ノート

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