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Sodium Hydroxide → HCID 178490931, 화합물

HRID 705345
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HRID 705345 반응식
ClC[CH2:3][N:4]1[C:8](=O)[O:7][N:6]=[C:5]1[C:10]1[C:14]2[CH:15]=[C:16]([CH:33]3[CH2:35][CH2:34]3)[C:17]([N:19]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]=2[O:12][C:11]=1[C:36]1[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=1.[OH-].[Na+]>C(O)C>[CH:33]1([C:16]2[C:17]([N:19]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=3)[S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][C:13]3[O:12][C:11]([C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=4)=[C:10]([C:5]4[NH:4][CH2:3][CH2:8][O:7][N:6]=4)[C:14]=3[CH:15]=2)[CH2:34][CH2:35]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 89955642HCID 89955642, 화합물

생성물 1

HCID 178490931HCID 178490931, 화합물수율 67%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of Example 8E (3.54 g, 5.78 mmol) and 1.0 M aqueous sodium hydroxide (14.46 mL, 14.46 mmol) in ethanol (50 mL) was refluxed for 2 hours, cooled, and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. The residue was purified on silica gel eluting with methanol (2% to 4%) in dichloromethane to give the title compound as a solid (2.13 g, 67%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.16-0.27 (m, 1H) 0.65-0.82 (m, 2H) 0.85-1.00 (m, 1H) 2.15-2.25 (m, 1H) 3.20 (s, 3H) 3.66-3.69 (m, 3H) 4.54 (s, 2H) 4.69-4.91 (m, 2H) 6.77-6.82 (m, 2H) 7.03 (s, 1H) 7.10-7.16 (m, 2H) 7.37-7.45 (m, 2H) 7.80 (s, 1H) 7.83-7.91 (m, 2H) 11.32 (s, 1H); MS (ESI+) m/z 550.1 (M+H)+.

후처리

  1. temperaturecooled
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel eluting with methanol (2% to 4%) in dichloromethane

출처 및 근거

ORD 기록
ord-1216a8bdd2444540a5363a3269b1e25a
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09173887B2

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