3-(Acetylthio)-2-[(acetylthio)methyl]propanoic acid → 2-hydroxy-3-mercaptopropanoyl-L-lysine

HRID 47145Notes

Reaction equation

HRID 47145 reaction equation
C(OC(CSC(=O)C)C(O)=O)(=[O:3])C.C(SCC(CSC(=O)C)C(O)=O)(=O)C.C([O:32][C:33](=[O:60])[C@H:34]([CH2:48][CH2:49][CH2:50][CH2:51][NH:52]C(OC(C)(C)C)=O)[NH:35][C:36](=[O:47])[CH:37](OC(=O)C)[CH2:38][S:39]C(=O)C)(C)(C)C.C(OC(CSC(=O)C)C(N[C@H](C(O)=O)CCCCN)=O)(=O)C>>[OH:3][C@@:34]([C:33]([OH:32])=[O:60])([CH2:48][CH2:49][CH2:50][CH2:51][NH2:52])[NH:35][C:36](=[O:47])[CH2:37][CH2:38][SH:39]

Participants

5

Reactant 4

HCID 131455313-(Acetylthio)-2-[(acetylthio)methyl]propanoic acidHCID 22805637HCID 22805637, compoundHCID 233361832-Acetoxy-3-(acetylthio)propanoic acidHCID 86736713Nalpha-[2-acetoxy-3-(acetylthio)propanoyl]-Nepsilon-tert.butyloxycarbonyl-L-lysine tert.butyl ester

Product 1

HCID 867367122-hydroxy-3-mercaptopropanoyl-L-lysine

Procedure

By substituting 2-acetoxy-3-(acetylthio)propanoic acid for the 2-(acetylthiomethyl)-3-(acetylthio)propanoic acid in the procedure of Example 38 and then submitting the product to the procedures of Examples 39 and 40, Nα -[2-acetoxy-3-(acetylthio)propanoyl]-Nε -tert.butyloxycarbonyl-L-lysine tert.butyl ester, Nα -[2-acetoxy-3-(acetylthio)propanoyl]-L-lysine and Nα -(2-hydroxy-3-mercaptopropanoyl-L-lysine are obtained.

Sources & evidence

ORD record
ord-af0e3f842c9d4425a1e9851b048fb829
Source dataset
uspto-grants-1979_11
Patent number
US04176235

Reaction notes

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