Hydrochloric Acid → Leucyl-phenylalanine amide

HRID 1768869Notes

Reaction equation

HRID 1768869 reaction equation
[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]

Participants

4

Reactant 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

Product 1

HCID 3082491Leucyl-phenylalanine amideYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-98a9155ea31a457a98cd3c88e1ce2607
Source dataset
uspto-grants-1995_01
Patent number
US05378803

Reaction notes

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