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

HRID 1061209
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HRID 1061209 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매
HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6fda2c8b8198495aacca7e5e58c3f311
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06525202B2

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