(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 397759Notes

Reaction equation

HRID 397759 reaction equation
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.[CH3:52][C:53]1[CH:58]=[CH:57][C:56]([S:59]([N:62]([C@H:67]([C:99]([OH:101])=[O:100])[CH2:68][CH2:69][CH2:70][CH2:71][NH:72][C:73]([C@@H:75]([NH:86][S:87]([C:90]2[CH:95]=[CH:94][C:93]([N+:96]([O-])=O)=[CH:92][CH:91]=2)(=[O:89])=[O:88])[CH2:76][C:77]2[C:85]3[C:80](=[CH:81][CH:82]=[CH:83][CH:84]=3)[NH:79][CH:78]=2)=[O:74])[CH2:63][CH:64]([CH3:66])[CH3:65])(=[O:61])=[O:60])=[CH:55][CH:54]=1>>[CH3:52][C:53]1[CH:54]=[CH:55][C:56]([S:59]([N:62]([C@H:67]([C:99]([OH:101])=[O:100])[CH2:68][CH2:69][CH2:70][CH2:71][NH:72][C:73]([C@@H:75]([NH:86][S:87]([C:90]2[CH:91]=[CH:92][C:93]([NH2:96])=[CH:94][CH:95]=2)(=[O:88])=[O:89])[CH2:76][C:77]2[C:85]3[C:80](=[CH:81][CH:82]=[CH:83][CH:84]=3)[NH:79][CH:78]=2)=[O:74])[CH2:63][CH:64]([CH3:66])[CH3:65])(=[O:60])=[O:61])=[CH:57][CH:58]=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 23552860Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine

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 hydroclloride (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-511cb463996845018b2d47456ae760c2
Source dataset
uspto-grants-2003_08
Patent number
US06610689B2

Reaction notes

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