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Benzenesulfonyl chloride → Benzoic acid 3-benzenesulfonylamino-4-benzyloxy-phenyl ester

HRID 1794710
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HRID 1794710 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(OCC)(=O)C.N1C=CC=CC=1>[C:25]1([S:31]([NH:1][C:2]2[CH:3]=[C:4]([O:16][C:17](=[O:24])[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:5]=[CH:6][C:7]=2[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
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참가 물질

5

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 86584542Benzoic acid 3-amino-4-benzyloxy-phenyl ester

생성물 1

HCID 86584543Benzoic acid 3-benzenesulfonylamino-4-benzyloxy-phenyl ester수율 61%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매2회

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온도
0 °C

실험 절차

To a stirred solution of benzoic acid 3-amino-4-benzyloxy-phenyl ester (5.91 g, 18.5 mmol) (which was obtained in Example 16) in ethyl acetate (100 mL) and pyridine (20 mL) at 0° C. was added dropwise phenyl sulfonyl chloride (3.26 g, 18.5 mmol) in 50 mL of ethyl acetate. After one hour at 0° C. the mixture was warmed to room temperature and stirred at room temperature over night. The reaction mixture was washed with water and the organic layer was dried (MgSO4) and concentrated. Recrystallization from CH2Cl2/hexanes gave the title compound as a white solid (4.65 g, 61%); 1H NMR (300 MHz, CDCl3) δ 4.93(s, 2 H), 6.90–7.80(m, 15 H), 8.12(d, J=8.5 Hz, 2 H), 9.81(s, 1 H); MS (ES) m/z: 458.9 (MH+, 100%); HRMS Calcd. for C26H22NO5S(MH+): 459.1141. Found: 459.1151.

후처리

  1. washThe reaction mixture was washed with water
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customRecrystallization from CH2Cl2/hexanes

출처 및 근거

ORD 기록
ord-2f6de172c2444ee6b8d7efdbba7dac34
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07022716B2

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