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Hydrochloric Acid → N-Benzyl-N-(2-benzyloxy-5-hydroxy-phenyl)-benzenesulfonamide

HRID 1061209
ノート
印刷プレビュー

反応式

HRID 1061209 の反応式
[C:1]1([S:7]([N:10]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:11]2[CH:12]=[C:13]([O:25]C(=O)C3C=CC=CC=3)[CH:14]=[CH:15][C:16]=2[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C1COCC1.CO.O>[CH2:34]([N:10]([C:11]1[CH:12]=[C:13]([OH:25])[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:9])=[O:8])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86584544Benzoic acid 3-(benzenesulfonyl-benzyl-amino)-4-benzyloxy-phenyl ester

生成物 1

HCID 22220539N-Benzyl-N-(2-benzyloxy-5-hydroxy-phenyl)-benzenesulfonamide収率 82.1%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒
HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of benzoic acid 3-(benzenesulfonyl-benzyl-amino)-4-benzyloxy-phenyl ester (which was obtained in Example 18) (1.80 g, 3.28 mmol) in THF (10 mL) and methanol (10 mL) was added 10% of sodium hydroxide (10 mL). The mixture was stirred at room temperature for 1.5 hours, acidified with concentrated hydrochloric acid and diluted with water (200 mL). The aqueous solution was extracted with CH2Cl2. The organic phase was dried over MgSO4 and concentrated. The product was purified by flash silica gel chromatography eluting with ethyl acetate and hexanes to give the title compound as a white solid (1.20 g, 82%); 1H NMR (300 MHz, CDCl3) δ 4.71 (brs, 4H), 6.49 (d, J=3.0 Hz, 1H), 6.62(dd, J=9.0, 3.0 Hz, 1H), 6.84 (d, J=9.0 Hz, 1H), 7.10-7.70 (m, 15H), 9.07 (brs, 1H); MS (ES) m/z: 444.0 ((M−H)−, 100%); HRMS Calcd. for C26H22NO4S(M−H)−: 444.1275. Found: 444.1270.

後処理

  1. extractionThe aqueous solution was extracted with CH2Cl2
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customThe product was purified by flash silica gel chromatography
  5. washeluting with ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-6fda2c8b8198495aacca7e5e58c3f311
出典データセット
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06525202B2

反応ノート

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