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Lithium hydroxide, monohydrate → 6-(Benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoic acid

HRID 2177784
ノート
印刷プレビュー

反応式

HRID 2177784 の反応式
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19]C)=[O:18])=[C:15]([NH:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:14]([C:32]3[CH:36]=[CH:35][O:34][CH:33]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>O.O1CCOCC1>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([NH:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[C:14]([C:32]3[CH:36]=[CH:35][O:34][CH:33]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
参加物反応条件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 168937Lithium hydroxide, monohydrateHCID 67108007Methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoate2 回

生成物 1

HCID 671077416-(Benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)ethylamino]-3-(furan-3-yl)benzoic acid収率 89.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回
HCID 31275
1,4-Dioxane
溶媒

反応条件

温度
100 °C

実験手順

Methyl 6-(benzenesulphonylmethyl)-2-[2-(t-butoxycarbonylamino)-ethylamino]-3-(furan-3-yl)benzoate (Intermediate 122, 0.115 g) was added to a solution of lithium hydroxide monohydrate (0.168 g) in water (1 ml) and dioxane (3 ml) and the mixture was heated at 100° C. for 1 hour. The reaction was cooled to room temperature, diluted with water and washed with diethyl ether. The aqueous layer was acidified with acetic acid and extracted with ethyl acetate, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM:MeOH:AcOH:water (350:20:3:2) to give 6-(benzenesulphonylmethyl)-2-[2-(tert-butoxycarbonylamino)-ethylamino]-3-(furan-3-yl)benzoic acid (0.1 g) as a pale yellow gum.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of DCM:MeOH:AcOH:water (350:20:3:2)

出典と根拠

ORDレコード
ord-5457a007b60b4146b84938649f56d6d3
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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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート