Sodium Thiosulfate → HCID 9916656, compound

HRID 1830163Notes

Reaction equation

HRID 1830163 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C@@H:12]([NH:16][C:17](=[O:41])[CH:18]([CH2:30][S:31]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:33])=[O:32])[CH2:19][S:20]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:22])=[O:21])[CH2:13][CH2:14][CH3:15])[OH:11].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C@@H:12]([NH:16][C:17](=[O:41])[CH:18]([CH2:30][S:31]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:32])=[O:33])[CH2:19][S:20]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:22])=[O:21])[CH2:13][CH2:14][CH3:15])=[O:11]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 69436167HCID 69436167, compound

Product 1

HCID 9916656HCID 9916656, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[(S)-1-(1-Benzooxazol-2-yl-1-hydroxy-methyl)-butyl]-3-benzylsulfonyl-2-benzylsulfonylmethyl-propionamide (0.140 g, 0.234 mmol) in methylene chloride (5 mL) was treated with 1,1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (Dess-Martin periodinane) (0.127 g, 0.30 mmol.) and the resulting solution was stirred at room temperature for 30 minutes. Aqueous sodium thiosulfate and sodium bicarbonate (15 mL, 0.25 M) were added and the reaction mixture was stirred for 20 minutes. The product was extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium chloride and then dried over magnesium sulfate. The solvent was removed by rotary evaporation at reduced pressure and the residue was crystallized from t-butylmethyl ether to give N-[(S)-1-(1-benzooxazol-2-yl-methanoyl)-butyl]-3-benzylsulfonyl-2-benzylsulfonylmethyl-propionamide (0.103 g, 74%); NMR (DMSO): 9.15 (d, J=6 Hz, 1H); 8.01 (d, J=7 Hz, 1H); 7.89 (d, J=8 Hz, 1H); 7.65 (t, J=7 Hz, 1H); 7.54 (t, J=8 Hz, 1H); 7.37 (m, 10H); 5.36 (m, 1H); 4.5 (m, 4H); 3.68 (m, 1H); 3.45–3.25 (m, 4H); 1.95 (m, 1H); 1.73 (m, 1H); 1.47 (m, 2H); 0.91 (t, J=7 Hz, 3H); MS: M(H+) 597.0 (596.17);

Workup

  1. stirringthe reaction mixture was stirred for 20 minutes
  2. extractionThe product was extracted with ethyl acetate
  3. washThe extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by rotary evaporation at reduced pressure
  6. customthe residue was crystallized from t-butylmethyl ether

Sources & evidence

ORD record
ord-b1cba379b9b5404a8c6e4c5ae012555d
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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