L-Lysine → Nalpha-(4-carboxy-2-methylbutanoyl)-L-lysine

HRID 262277Notes

Reaction equation

HRID 262277 reaction equation
C(OC(=O)[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:56]([O:58]C)=[O:57])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:56]([CH2:55][CH2:54][CH:53]([CH3:60])[C:52]([NH:51][C@H:50]([C:49]([OH:77])=[O:48])[CH2:62][CH2:63][CH2:64][CH2:65][NH2:66])=[O:61])([OH:58])=[O:57]

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 22804611Nalpha-(4-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 procedure 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-edb5558598fe4bb1869d0dc23ea36e0c
Source dataset
uspto-grants-1979_05
Patent number
US04153725

Reaction notes

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