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Hydrochloric Acid → Methyl 2-(3-aminopropyl)-6-(benzenesulphonylmethyl)-3-(furan-3-yl)benzoate

HRID 2177679
ノート
印刷プレビュー

反応式

HRID 2177679 の反応式
Cl.[C:2]1([S:8]([CH2:11][C:12]2[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]([CH2:22][CH2:23][CH2:24][NH:25]C(OC(C)(C)C)=O)[C:15]([C:33]3[CH:37]=[CH:36][O:35][CH:34]=3)=[CH:14][CH:13]=2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.O>[NH2:25][CH2:24][CH2:23][CH2:22][C:16]1[C:15]([C:33]2[CH:37]=[CH:36][O:35][CH:34]=2)=[CH:14][CH:13]=[C:12]([CH2:11][S:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)(=[O:10])=[O:9])[C:17]=1[C:18]([O:20][CH3:21])=[O:19]
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 313Hydrochloric AcidHCID 67107639Methyl 6-(benzenesulphonylmethyl)-2-(3-t-butoxycarbonylaminopropyl)-3-(furan-3-yl)benzoate2 回

生成物 1

HCID 67108214Methyl 2-(3-aminopropyl)-6-(benzenesulphonylmethyl)-3-(furan-3-yl)benzoate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

Concentrated hydrochloric acid was added to a solution of methyl 6-(benzenesulphonylmethyl)-2-(3-t-butoxycarbonylaminopropyl)-3-(furan-3-yl)benzoate (Intermediate 131) in 1,4-dioxane (8 ml) and water (2 ml) and the mixture was stirred for 30 minutes. This was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of DCM:MeOH:AcOH:water (120:15:3:2) to give methyl 2-(3-aminopropyl)-6-(benzenesulphonylmethyl)-3-(furan-3-yl)benzoate as a colourless gum. This material was dissolved in a mixture of dioxane and water (3:1) and lithium hydroxide monohydrate (0.188 g) was added. The reaction was heated in the microwave at 150° C. for one hour. After cooling, concentrated hydrochloric acid was added and the mixture was evaporated to dryness. The residue was purified by chromatography on silica eluting with a mixture of DCM:MeOH:AcOH:water (240:20:3:2), then again with DCM:MeOH:AcOH:water (120:15:3:2). The volume of the product containing fractions was reduced to 5 ml by evaporation and concentrated hydrochloric acid (1 ml) was added to the mixture. The mixture was evaporated to dryness and the residue was triturated with diethyl ether and the solid was collected by filtration and dried under vacuum at 60° C. to give 2-(3-aminopropyl)-6-(benzenesulphonylmethyl)-3-(furan-3-yl)benzoic acid hydrochloride (0.045 g), as a white solid.

後処理

  1. customThis was evaporated to dryness
  2. customthe residue was purified by chromatography on silica eluting with a mixture of DCM:MeOH:AcOH:water (120:15:3:2)

出典と根拠

ORDレコード
ord-414612af89504fd59bed8b818170b824
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09067905B2

反応ノート

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