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

HRID 2419387Notes

Reaction equation

HRID 2419387 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:42][C:43]([CH2:45][CH2:46][CH:47]([CH3:60])[C:48]([NH:50][C@H:51]([C:57]([OH:59])=[O:58])[CH2:52][CH2:53][CH2:54][CH2:55][NH2:56])=[O:49])=[O:44].N[C@H](C(O)=O)CCCCN>>[C:43]([CH2:45][CH2:46][CH:47]([CH3:60])[C:48]([NH:50][C@H:51]([C:57]([OH:59])=[O:58])[CH2:52][CH2:53][CH2:54][CH2:55][NH2:56])=[O:49])([OH:44])=[O:42]

Participants

5

Reactant 4

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

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 procedures of Examples 24 and 26, Nα -(4-methoxycarbonyl-2-methylbutanoyl)-N68 -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-8554283c1cdb42e782bae8f923c09b77
Source dataset
uspto-grants-1978_08
Patent number
US04105789

Reaction notes

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