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

HRID 397774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397774
[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]

Komponenten

7

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7ab8f639491f4c47ad1e5f3c06cd0195
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610689B2

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