(2S)-6-[[(2S)-3-(1H-indol-3-yl)-2-[(4-nitrophenyl)sulfonylamino]propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid → (2S)-6-[[(2S)-2-[(4-aminophenyl)sulfonylamino]-3-(1H-indol-3-yl)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

HRID 1839484Notes

Reaction equation

HRID 1839484 reaction equation
Cl.C(N(S(C1C=CC(C)=CC=1)(=O)=O)[C@H](C(O)=O)CCCCN)C(C)C.[N+](C1C=CC(S(N[C@H](C(O)=O)CC2C3C(=CC=CC=3)NC=2)(=O)=O)=CC=1)([O-])=O.[CH3:53][C:54]1[CH:59]=[CH:58][C:57]([S:60]([N:63]([C@H:68]([C:100]([OH:102])=[O:101])[CH2:69][CH2:70][CH2:71][CH2:72][NH:73][C:74]([C@@H:76]([NH:87][S:88]([C:91]2[CH:96]=[CH:95][C:94]([N+:97]([O-])=O)=[CH:93][CH:92]=2)(=[O:90])=[O:89])[CH2:77][C:78]2[C:86]3[C:81](=[CH:82][CH:83]=[CH:84][CH:85]=3)[NH:80][CH:79]=2)=[O:75])[CH2:64][CH:65]([CH3:67])[CH3:66])(=[O:62])=[O:61])=[CH:56][CH:55]=1>>[CH3:53][C:54]1[CH:55]=[CH:56][C:57]([S:60]([N:63]([C@H:68]([C:100]([OH:102])=[O:101])[CH2:69][CH2:70][CH2:71][CH2:72][NH:73][C:74]([C@@H:76]([NH:87][S:88]([C:91]2[CH:92]=[CH:93][C:94]([NH2:97])=[CH:95][CH:96]=2)(=[O:89])=[O:90])[CH2:77][C:78]2[C:86]3[C:81](=[CH:82][CH:83]=[CH:84][CH:85]=3)[NH:80][CH:79]=2)=[O:75])[CH2:64][CH:65]([CH3:67])[CH3:66])(=[O:61])=[O:62])=[CH:58][CH:59]=1

Participants

4

Reactant 3

HCID 508531(2S)-6-[[(2S)-3-(1H-indol-3-yl)-2-[(4-nitrophenyl)sulfonylamino]propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acidHCID 1572095Nalpha(4-nitrobenzenesulfonyl)-L-tryptophanHCID 23552859Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine hydrochloride

Product 1

HCID 508536(2S)-6-[[(2S)-2-[(4-aminophenyl)sulfonylamino]-3-(1H-indol-3-yl)propanoyl]amino]-2-[isobutyl(p-tolylsulfonyl)amino]hexanoic acid

Procedure

The title compound was prepared from Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine hydrochloride (200 mg, 0.59 mmol, example 1, step E) as described in general procedure Bc using Nα-(4-nitrobenzenesulfonyl)-L-tryptophan (300 mg, 0.75 mmol) prepared in step A of example 5. The intermediate, Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-Nε-[N′α-(4-nitrobenzenesulfonyl)-L-tryptophanyl]-L-lysine, was reduced following the conditions of general procedure E. The final product was purified by preparative HPLC to yield 266 mg (58%) of the desired material.

Workup

  1. customThe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-f8ce656c17364bea88a10674fb6679b3
Source dataset
uspto-grants-2004_01
Patent number
US06677367B2

Reaction notes

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