Nalpha-[2-(acetylthiomethyl)-3-(acetylthio)propanoyl]-Nepsilon-tert.-butyloxycarbonyl-L-lysine tert.butyl ester → HCID 22805641, compound

HRID 1391104Notes

Reaction equation

HRID 1391104 reaction equation
C([O:5][C:6](=[O:34])[C@H:7]([CH2:22][CH2:23][CH2:24][CH2:25][NH:26]C(OC(C)(C)C)=O)[NH:8][C:9](=[O:21])[CH:10]([CH2:16][S:17][C:18](=[O:20])[CH3:19])[CH2:11][S:12][C:13](=[O:15])[CH3:14])(C)(C)C>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[C:13]([S:12][CH2:11][CH:10]([CH2:16][S:17][C:18](=[O:20])[CH3:19])[C:9]([NH:8][C@H:7]([C:6]([OH:34])=[O:5])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])=[O:21])(=[O:15])[CH3:14]

Participants

4

Reactant 1

HCID 86736038Nalpha-[2-(acetylthiomethyl)-3-(acetylthio)propanoyl]-Nepsilon-tert.-butyloxycarbonyl-L-lysine tert.butyl ester

Product 1

HCID 22805641HCID 22805641, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

Nα -[2-(acetylthiomethyl)-3-(acetylthio)propanoyl]-Nε -tert.butyloxycarbonyl-L-lysine tert.butyl ester (3 g.) is dissolved in a mixture of trifluoroacetic acid and anisole, and the mixture is stored at room temperature for one hour. The trifluoroacetic acid is removed in vacuo, the residue is distributed between ether and water and the aqueous layer is applied to a column of Dowex 50. After washing the acidic material with water, the Nα -[2-(acetylthiomethyl)-3-(acetylthio)propanoyl]-L-lysine is eluted with a buffer of pyridine-acetic acid at pH 6.5.

Workup

  1. customThe trifluoroacetic acid is removed in vacuo
  2. washAfter washing the acidic material with water
  3. washthe Nα -[2-(acetylthiomethyl)-3-(acetylthio)propanoyl]-L-lysine is eluted with a buffer of pyridine-acetic acid at pH 6.5

Sources & evidence

ORD record
ord-2b90c5c8122e45d49e6dea18a3df2f09
Source dataset
uspto-grants-1979_02
Patent number
US04140864

Reaction notes

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