Oxalyl chloride → HCID 17915532, compound

HRID 1107163Notes

Reaction equation

HRID 1107163 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 17915532HCID 17915532, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-e6549b80a82e4bbaab3bcd87bd594969
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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