Lithium Hydroxide → 2-{[(Tert-butoxycarbonyl)amino]sulfonyl}benzoic acid

HRID 1992122ノート

反応式

HRID 1992122 の反応式
[C:1]([O:5][C:6]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([O:16]C)=[O:15])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][S:9]([C:12]1[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=1[C:14]([OH:16])=[O:15])(=[O:10])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 14988086Methyl 2-{[(tert-butoxycarbonyl)amino]sulfonyl}benzoate

生成物 1

HCID 587286752-{[(Tert-butoxycarbonyl)amino]sulfonyl}benzoic acid収率 51.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of methyl 2-{[(tert-butoxycarbonyl)amino]sulfonyl}benzoate 1a (400 mg, 1.3 mmol, 1 equiv) and lithium hydroxide (1.6 g, 39 mmol, 30 equiv) in tetrahydrofuran (10 mL) and water (2.5 mL) was stirred at RT for 18 h. The reaction was partially concentrated, acidified with 1N HCl and the product extracted into ethyl acetate. The organic layer was dried and concentrated to afford 2-{[(tert-butoxy carbonyl)amino]sulfonyl}benzoic acid (1b) as a white solid (200 mg, 51% yield). 1H NMR (300 MHz, DMSO) δ 7.94 (m, 1H), 7.71 (m, 3H), 1.26 (s, 9H). ES-LCMS m/z 300.08 (M−H).

後処理

  1. concentrationThe reaction was partially concentrated
  2. extractionthe product extracted into ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-af7d7a1d297641efb3d2d0716df423e4
出典データセット
uspto-grants-2010_01
特許番号
US07645771B2

反応ノート

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