Hydrochloric Acid → N-hydroxy-2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxamide

HRID 1107130Notes

Reaction equation

HRID 1107130 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][C:12]2[C:16](=[CH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14][C:13]=2[C:26]([OH:28])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(Cl)(=O)C(Cl)=O.C[Si](C)(C)[O:37][NH2:38].Cl>ClCCl>[OH:37][NH:38][C:26]([C:13]1[CH2:14][CH2:15][C:16](=[CH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:12]=1[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:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 699076212-[(3,4-Dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylic acid

Product 1

HCID 86755387N-hydroxy-2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxylic acid (0.6 g, 1.5 mmol) in dichloromethane (20 mL) is added 2 M oxalyl chloride (1.5 mL, 3 mmol). The mixture is stirred at room temperature for 15 minutes. The solvent is removed in vacuo and the residue is dissolved in dichloromethane and O-(trimethylsilyl)hydroxylamine (0.3 mL, 3 mmol) is added. The mixture is stirred at room temperature for 30 minutes. The mixture is poured into 5% HCl and is extracted with dichloromethane. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo and the residue is chromatographed on silica gel (100% ethyl acetate). The product is dissolved in the minimum amount of ethyl acetate and the solution is diluted to the cloudy point with hexane to precipitate N-hydroxy-2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxamide on standing at room temperature overnight (0.1 g, 16%): m.p. 44-6° C. Anal. (C23H27NO4S.1/4H2O) C,H,N: 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.42-1.78 (m, 5H), 1.90-2.08 (m, 1H), 2.38-2.50 (m, 2H), 2.59-2.78 (m, 3H), 3.82 (s, 3H), 3.90 (s, 3H), 6.72-6.79 (d, 1H), 6.88-6.98 (m, 2H), 6.98-7.10 (d, 2H), 7.10-7.30 (m, 3H), 9.02 (s, 1H); MS (Ion Spray) m/e 413 (M+H)+.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe residue is dissolved in dichloromethane
  3. stirringThe mixture is stirred at room temperature for 30 minutes
  4. extractionis extracted with dichloromethane
  5. washThe organic layer is washed with water
  6. dry with materialis dried over MgSO4
  7. customThe solvent is removed in vacuo
  8. customthe residue is chromatographed on silica gel (100% ethyl acetate)
  9. dissolutionThe product is dissolved in the minimum amount of ethyl acetate
  10. additionthe solution is diluted to the cloudy point with hexane
  11. customto precipitate N-hydroxy-2-[(3,4-dimethoxyphenyl)thio]-3-(3-phenylpropyl-1-yl)-1-cyclopentenecarboxamide
  12. waiton standing at room temperature overnight

Sources & evidence

ORD record
ord-d2d931b5633343cea97471c0eae4d837
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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