Oxalyl chloride → 1-[1-(3,4-Dimethoxyphenylsulfonyl)-5-phenylpentyl]cyclopentanecarboxylic acid hydroxyamide

HRID 1107157Notes

Reaction equation

HRID 1107157 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([CH:14]([C:25]2([C:30]([OH:32])=O)[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(Cl)(=O)C(Cl)=O.C[Si]([NH:43][OH:44])(C)C>C(Cl)Cl>[OH:44][NH:43][C:30]([C:25]1([CH:14]([S:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)(=[O:13])=[O:12])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:32]

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 187900681-[1-(3,4-Dimethoxyphenylsulfonyl)-5-phenylpentyl]cyclopentane carboxylic acidHCID 21936899N-Hydroxy-1,1,1-trimethylsilanamine

Product 1

HCID 187901611-[1-(3,4-Dimethoxyphenylsulfonyl)-5-phenylpentyl]cyclopentanecarboxylic acid hydroxyamideYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1-[1-(3,4-Dimethoxyphenylsulfonyl)-5-phenylpentyl]cyclopentane carboxylic acid (0.69 g, 1.5 mmol) is dissolved in CH2Cl2 (6 mL), cooled to 0° C. and 2 M oxalyl chloride in CH2Cl2 (2.2 mL, 4.4 mmol) is added. The reaction is warmed and stirred at room temperature 2 hours. The solvent is removed in vacuo and the residue azeotroped with chloroform (2×10 mL). The residue is dissolved in CH2Cl2 (2 mL) and cooled to 0° C. Trimethylsilylhydroxylamine (0.52 mL, 4.5 mmol) is added over 1 minute and this mixture is stirred 5 minutes. Then the ice bath is removed and the reaction stirred at room temperature overnight. The solvent is removed in vacuo and CH2Cl2 (20 mL) added and the solution washed with 1 N HCl (20 mL). The solution is dried over MgSO4 and the solvent removed in vacuo to give 1-[1-(3,4-Dimethoxyphenylsulfonyl)-5-phenylpentyl]cyclopentanecarboxylic acid hydroxyamide (0.48 g, 67%): 1H NMR (300 MHz, CD3OD) δ 7.44 (dd, J=8.3, 2.0 Hz, 1H), 7.36 (d, J=2.3 Hz, 1H), 7.22-7.05 (m, 4H), 6.98 (d, J=7.0 Hz, 2H), 3.89 (s, 3H), 3.87 (m, 4H), 2.38 (t, J=7.4 Hz, 2H), 2.35-2.25 (m, 1H), 1.96-1.63 (m, 10H), 1.34-1.27 (m, 2H), 1.21-1.10 (m, 1H), 1.00-0.88 (m, 1H); MS (EI) m/e 476 (M+).

Workup

  1. temperatureThe reaction is warmed
  2. customThe solvent is removed in vacuo
  3. customthe residue azeotroped with chloroform (2×10 mL)
  4. dissolutionThe residue is dissolved in CH2Cl2 (2 mL)
  5. temperaturecooled to 0° C
  6. stirringthis mixture is stirred 5 minutes
  7. customThen the ice bath is removed
  8. stirringthe reaction stirred at room temperature overnight
  9. customThe solvent is removed in vacuo and CH2Cl2 (20 mL)
  10. additionadded
  11. washthe solution washed with 1 N HCl (20 mL)
  12. dry with materialThe solution is dried over MgSO4
  13. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4ec1576c983e47afb347a439fba24010
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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