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

HRID 47142Notes

Reaction equation

HRID 47142 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 pyridineacetic 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 pyridineacetic acid at pH 6.5

Sources & evidence

ORD record
ord-489165b9e70340bdbd6ac521d1ed1ad1
Source dataset
uspto-grants-1979_11
Patent number
US04176235

Reaction notes

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