Sodium Thiosulfate → HCID 67300896, compound
Reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[S:23]1[CH:27]=[N:26][N:25]=[C:24]1[CH:28]([OH:46])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].[O-]S([O-])(=S)=O.[Na+].[Na+].CO.C(Cl)Cl>C(Cl)Cl.CCOCC.C([O-])(O)=O.[Na+]>[S:23]1[CH:27]=[N:26][N:25]=[C:24]1[C:28](=[O:46])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[CH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
(141) A suspension of the Dess-Martin periodinane (1.2 equiv, 0.013 mmol, 14 mg) in anhydrous CH2Cl2(0.5 mL) was treated with a solution of 1-([1,3,4]thiadiazol-2-yl)octadec-9-en-1-ol (4 mg, 0.011 mmol) in anhydrous CH2Cl2 (0.5 mL) at rt under N2. After 10 h the suspension was diluted with Et2O (10 mL), and poured into a solution of Na2S2O3 (40 mg) in saturated aqueous NaHCO3 (3.4 mL). The mixture was stirred at rt for 1 h and the layers were separated. The ethereal layer was washed with saturated aqueous NaHCO3 (1×10 mL) and H2O (1×10 mL), dried (MgSO4), filtered and evaporated. Flash chromatography (SiO2, 1.5 cm×15 cm, 2% MeOH—CH2Cl2) afforded 1-([1,3,4]thiadiazol-2-yl)octadec-9-en-1-one (141) (3 mg, 0.008 mmol, 70% yield) as a dark yellow oil: MALDI-FTMS (DHB) m/z 351.2464 (C20H34N2OS+H+ requires 351.2470).
Workup
- customthe layers were separated
- washThe ethereal layer was washed with saturated aqueous NaHCO3 (1×10 mL) and H2O (1×10 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-020c43dc3a3f495e96d3b5b5b95ffd48
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662971B2
Reaction notes
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