L-Lysine → 4-carboxy-2-methylbutanoyl-L-lysine

HRID 1701366Notes

Reaction equation

HRID 1701366 reaction equation
C([O:8][C:9](=[O:27])[C@H](CCCCNC(OCC1C=CC=CC=1)=O)N)C1C=CC=CC=1.C(OC(=O)[C@H](C)N)C1C=CC=CC=1.C([O:48][C:49](=[O:77])[C@H:50]([CH2:62][CH2:63][CH2:64][CH2:65][NH:66]C(OCC1C=CC=CC=1)=O)[NH:51][C:52](=[O:61])[CH:53]([CH3:60])[CH2:54][CH2:55]C(OC)=O)C1C=CC=CC=1.COC(CCC(C)C(N[C@H](C(O)=O)CCCCN)=O)=O.N[C@H](C(O)=O)CCCCN>>[C:9]([CH:63]([CH2:64][CH2:65][NH2:66])[CH2:62][C@@H:50]([C:49]([OH:48])=[O:77])[NH:51][C:52](=[O:61])[CH:53]([CH3:60])[CH2:54][CH3:55])([OH:27])=[O:8]

Participants

6

Reactant 5

HCID 5962L-LysineHCID 726858benzyl (2S)-2-aminopropanoateHCID 7269426benzyl (2S)-2-amino-6-(phenylmethoxycarbonylamino)hexanoateHCID 22804617Nalpha-(4-methoxycarbonyl-2-methylbutanoyl)-L-lysineHCID 86736432Nalpha-(4-methoxycarbonyl-2-methylbutanoyl)-Nepsilon-benzyloxycarbonyl-L-lysine benzyl ester

Product 1

HCID 867368614-carboxy-2-methylbutanoyl-L-lysine

Procedure

By substituting Nε -benzyloxycarbonyl-L-lysine benzyl ester for the L-alanine benzyl ester in the procedure of Example 23 and then treating the product by the procedures of Examples 24 and 26, Nα -(4-methoxycarbonyl-2-methylbutanoyl)-Nε -benzyloxycarbonyl-L-lysine benzyl ester, Nα -(4-methoxycarbonyl-2-methylbutanoyl)-L-lysine and Nα -(4-carboxy)-2-methylbutanoyl)-L-lysine are obtained.

Workup

  1. customare obtained

Sources & evidence

ORD record
ord-86bf70b7eb4a4004b7aaeba0028bf5f7
Source dataset
uspto-grants-1980_03
Patent number
US04192881

Reaction notes

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