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

HRID 1634657ノート

反応式

HRID 1634657 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6cc6e469e7d94067be58e36062fdb3d5
出典データセット
uspto-grants-2003_01
特許番号
US06506786B2

反応ノート

読み込み中…