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4-Toluenesulfonyl chloride → HCID 86709661、化合物

HRID 2285366
ノート
印刷プレビュー

反応式

HRID 2285366 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C@H:12]([NH:14][C:15]([C@@H:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:43])[C@@H:24]([NH:26][C:27](=[O:42])[C@@H:28]([NH:32][C:33](=[O:41])[C:34]([CH2:38][CH2:39]O)([CH3:37])[CH:35]=[CH2:36])[CH:29]([CH3:31])[CH3:30])[CH3:25])[NH:18]3)=[O:16])[CH3:13])=[N:9]2)=[CH:4][CH:3]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C@H:12]([NH:14][C:15]([C@@H:17]3[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:43])[C@@H:24]([NH:26][C:27](=[O:42])[C@@H:28]([N:32]4[CH2:36][CH2:35][C:34]([CH3:37])([CH:38]=[CH2:39])[C:33]4=[O:41])[CH:29]([CH3:31])[CH3:30])[CH3:25])[NH:18]3)=[O:16])[CH3:13])=[N:9]2)=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 73974-Toluenesulfonyl chloride2 回HCID 86709659(S)-1-((S)-2-{(S)-2-[2-(2-Hydroxy-ethyl)-2-methyl-but-3-enoylamino]-3-methyl-butyrylamino}-propionyl)-hexahydro-pyridazine-3-carboxylic acid [(R)-1-(7-bromo-quinolin-2-yl)-ethyl]-amide

生成物 1

HCID 86709661HCID 86709661、化合物収率 42.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒2 回
HCID 6344Dichloromethane溶媒

実験手順

A solution of (S)-1-((S)-2-{(S)-2-[2-(2-hydroxy-ethyl)-2-methyl-but-3-enoylamino]-3-methyl-butyrylamino}-propionyl)-hexahydro-pyridazine-3-carboxylic acid [(R)-1-(7-bromo-quinolin-2-yl)-ethyl]-amide (186.4 mg, 0.282 mmol) and 4-dimethylaminopyridine (206.7 mg, 1.692 mmol) in dichloromethane (20 mL) was treated with para-toluenesulfonyl chloride (161.6 mg, 0.848 mmol). After stirring at room temperature for 2.5 h, more 4-dimethylaminopyridine (206.7 mg, 1.692 mmol) and para-toluenesulfonyl chloride (161.6 mg, 0.848 mmol) were added. After stirring at room temperature for 1.5 h, the volatiles were removed in vacuo. The residue was purified by silica gel chromatography using a 20 g Isolute cartridge eluted with a continuous gradient of iso-hexanes/acetone 1:0 to 3:2 to afford the title compound (77.0 mg, 42%) as a colourless gum and as a 1:1 mixture of diastereoisomers. LCMS (m/z) 643.1 [M+H], Tr=1.90 min and LCMS (m/z) 643.1 [M+H], Tr=1.99 min.

後処理

  1. stirringAfter stirring at room temperature for 1.5 h
  2. customthe volatiles were removed in vacuo
  3. customThe residue was purified by silica gel chromatography
  4. washeluted with a continuous gradient of iso-hexanes/acetone 1:0 to 3:2

出典と根拠

ORDレコード
ord-9b196e2be4f842e2b2177c870da0c130
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09145441B2

反応ノート

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