4-Nitrophenol → (2S)-N-[(5S)-5-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-hydrazino-6-oxo-hexyl]-3-phenyl-2-(2-thienylsulfonylamino)propanamide

HRID 396892Notes

Reaction equation

HRID 396892 reaction equation
[CH3:1][CH:2]([CH2:4][N:5]([S:34]([C:37]1[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=1)(=[O:36])=[O:35])[C@H:6]([C:31]([OH:33])=O)[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C@@H:14]([NH:22][S:23]([C:26]1[S:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:3].C1C([N+]([O-])=O)=CC=C(O)C=1.C1CCC(N=C=NC2CCCCC2)CC1.O.[NH2:70][NH2:71]>CCOC(C)=O.C(O)C>[CH3:3][CH:2]([CH2:4][N:5]([S:34]([C:37]1[CH:42]=[CH:41][C:40]([NH2:43])=[CH:39][CH:38]=1)(=[O:36])=[O:35])[C@H:6]([C:31]([NH:70][NH2:71])=[O:33])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C@@H:14]([NH:22][S:23]([C:26]1[S:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24])[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH3:1]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 24654Hydrazine hydrate (1:1)HCID 508569(2S)-2-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-[[(2S)-3-phenyl-2-(2-thienylsulfonylamino)propanoyl]amino]hexanoic acid

Product 1

HCID 508572(2S)-N-[(5S)-5-[(4-aminophenyl)sulfonyl-isobutyl-amino]-6-hydrazino-6-oxo-hexyl]-3-phenyl-2-(2-thienylsulfonylamino)propanamideYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Nα-(4-aminobenzenesulfonyl)-Nα-isobutyl-Nε-[N′α-(2-thiophenesulfonyl)-L-phenylalanyl]-L-lysine (650 mg, 1.0 mmol, example 46) dissolved in EtOAc (20 mL) was treated with p-nitrophenol (139 mg, 1.0 mmol) and DCC (206 mg, 1.0 mmol) and was left in a refrigerator overnight. Afterwards, the precipitate was filtered off through celite and the solvent evaporated. The crude residue was used without further purification. A portion of the residue (55 mg, 0.072 mmol) was added to a solution of hydrazine hydrate in ethanol (1M, 10 mL). The resulting solution was stirred for 3 h before evaporation of the solvent. The residue was purified by preparative HPLC to yield 25 mg, 30% of the desired material.

Workup

  1. filtrationAfterwards, the precipitate was filtered off through celite
  2. customthe solvent evaporated
  3. customThe crude residue was used without further purification
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b32e816e9f5b490bb20e6b5f80f6494f
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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