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

HRID 1992122노트

반응식

HRID 1992122 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-af7d7a1d297641efb3d2d0716df423e4
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645771B2

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