Oxalyl chloride → HCID 17915532, 화합물

HRID 1107163노트

반응식

HRID 1107163 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([CH:14]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:15]([CH3:20])([CH3:19])[C:16](O)=[O:17])(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(Cl)(=O)C(Cl)=O.C[Si]([NH:41][OH:42])(C)C>C(Cl)Cl>[OH:42][NH:41][C:16](=[O:17])[C:15]([CH3:20])([CH3:19])[CH:14]([S:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:13])=[O:12])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

5

반응물 3

HCID 65578Oxalyl chlorideHCID 18790105HCID 18790105, 화합물HCID 21936899N-Hydroxy-1,1,1-trimethylsilanamine

생성물 1

HCID 17915532HCID 17915532, 화합물수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

3-(3,4-Dimethoxyphenylsulfonyl)-2,2-dimethyl-7-phenylheptanoic acid (0.5 g, 1.2 mmol) is dissolved in CH2Cl2 (6 mL), cooled in ice and 2 M oxalyl chloride in CH2Cl2 (1.7 mL, 3.5 mmol) is added. The reaction is warmed to room temperature and after 4 hours the solvent is removed in vacuo and the residue azeotroped twice with chloroform. The residue is dissolved in CH2Cl2 (4 mL) and trimethylsilylhydroxylamine (0.42 mL, 3.6 mmol) is added. The reaction is stirred 15 minutes and then the solvent is removed in vacuo, CH2Cl2 (10 mL) added and the solution washed with 1 N HCl. The organic layer is dried over MgSO4 and the solvent removed in vacuo to yield 3-(3,4-dimethoxybenzenesulfonyl)-2,2-dimethyl-7-phenylheptanoic acid hydroxyamide (0.34 g, 83%): 1H NMR (300 MHz, CD3OD) δ 7.45 (dd, J=8.3, 2.0 Hz, 1H), 7.38 (d, J=2.2 Hz, 1H), 7.21-7.05 (m, 4H), 6.98-6.95 (m, 2H), 3.89 (s, 3H), 3.88 (s, 3H), 3.86-3.84 (m, 1H), 2.38-2.33 (m, 2H), 1.93-1.84 (m, 1H), 1.69-1.64 (m, 1H), 1.43 (s, 3H), 1.34-1.23 (m, 3H), 1.23 (s, 3H), 0.98-0.85 (m, 1H); MS (FAB) m/e 450 (M+H)+.

후처리

  1. temperaturecooled in ice
  2. customis removed in vacuo
  3. customthe residue azeotroped twice with chloroform
  4. dissolutionThe residue is dissolved in CH2Cl2 (4 mL)
  5. customthe solvent is removed in vacuo, CH2Cl2 (10 mL)
  6. additionadded
  7. washthe solution washed with 1 N HCl
  8. dry with materialThe organic layer is dried over MgSO4
  9. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-e6549b80a82e4bbaab3bcd87bd594969
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057369

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