Sodium Hydroxide → 4-((4-hydroxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)-benzoic acid

HRID 1686255ノート

反応式

HRID 1686255 の反応式
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([CH2:24][C:25]2[CH:34]=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][CH:26]=2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+]>C1COCC1>[OH:4][C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])(=[O:12])=[O:13])=[CH:9][CH:10]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 66974740methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate

生成物 1

HCID 252072894-((4-hydroxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)-benzoic acid収率 15%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 4-((4-acetoxy-N-(2-methoxybenzyl)phenylsulfonamido)methyl)benzoate (crude) was dissolved in THF (1.0 mL) and treated with aqueous NaOH (1N, 2.0 mL, 2.0 mmol). The mixture was refluxed for an hour. Upon completion the THF was removed in vacuo and the resulting aqueous solution was acidified with 6 N aq HCl to a pH of ˜3. The aqueous phase was extracted with EtOAc (2×15 mL) and the combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The crude product was purified by reverse phase HPLC to afford 10.8 mg of the title compound (15% yield over two steps). MS (M−H, 426.1); 1H NMR (400 MHz, acetone-d6): δ, ppm: 3.65 (s, 3H), 4.37 (s, 2H), 4.43 (s, 2H), 6.79 (m, 2H), 7.01 (d, 2H, J=8.0 Hz), 7.17 (m, 2H), 7.28 (d, 2H, J=7.9 Hz), 7.73 (d, 2H, J=8.0 Hz), 7.87 (d, 2H, J=7.9 Hz).

後処理

  1. temperatureThe mixture was refluxed for an hour
  2. customUpon completion the THF was removed in vacuo
  3. extractionThe aqueous phase was extracted with EtOAc (2×15 mL)
  4. washthe combined organic layers were washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by reverse phase HPLC

出典と根拠

ORDレコード
ord-88a81f3455f449d687fe8632970923e0
出典データセット
uspto-grants-2012_04
特許番号
US08148544B2

反応ノート

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