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Benzyl Chloride → Benzoic acid 3-(benzenesulfonyl-benzyl-amino)-4-benzyloxy-phenyl ester

HRID 1061208
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HRID 1061208 반응식
[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([O:25][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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.[H-].[Na+].[H][H].[CH2:38](Cl)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C>[C:1]1([S:7]([N:10]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:11]2[CH:12]=[C:13]([O:25][C:26](=[O:33])[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=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:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
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참가 물질

6

반응물 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 86584543Benzoic acid 3-benzenesulfonylamino-4-benzyloxy-phenyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 86584544Benzoic acid 3-(benzenesulfonyl-benzyl-amino)-4-benzyloxy-phenyl ester수율 70%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

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온도
70 °C

실험 절차

To a stirred solution of benzoic acid 3-benzenesulfonylamino-4-benzyloxy-phenyl ester (which was obtained in Example 17) (2.88 g, 7.27 mmol) in DMF (20 mL) was added 60% sodium hydride (0.32 g, 8 mmol). After hydrogen evolution had subsided the stirred mixture was heated at 70° C. for 15 minute, and then it was cooled down to room temperature and a solution of benzyl chloride (1.01 g, 8 mmol) in 5 mL of DMF was added dropwise. The mixture was then heated at 85-90° C. for 2 hours, then it was cooled down to room temperature, poured into ice-water. The aqueous layer was extracted with ethyl acetate and the organic layer was dried 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 (2.40 g, 70%); 1H NMR (300 MHz, CDCl3) δ 4.74 (s, 2H), 4.83 (s, 2H), 8.83 (d, J=8.9 Hz, 1H), 8.10-8.50 (m, 2H); HRMS Calcd. for C33H28NO5S(MH+): 550.1688. Found: 550.1680.

후처리

  1. temperatureit was cooled down to room temperature
  2. temperatureThe mixture was then heated at 85-90° C. for 2 hours
  3. temperatureit was cooled down to room temperature
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. customthe organic layer was dried
  6. concentrationconcentrated
  7. customThe product was purified by flash silica gel chromatography
  8. washeluting with ethyl acetate and hexanes

출처 및 근거

ORD 기록
ord-0d673932e26a4f948b236b5dbb469526
출처 데이터셋
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06525202B2

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