Sodium Thiosulfate → HCID 67300896, compound

HRID 877409Notes

Reaction equation

HRID 877409 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

8

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 21226129Dichloromethane methanolHCID 67300868HCID 67300868, compound

Product 1

HCID 67300896HCID 67300896, compoundYield 77.8%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

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 (Z)-1-(1,3,4-thiadiazol-2-yl)-octadec-9-en-1-ol (4 mg, 0.011 mmol) in anhydrous CH2Cl2 (0.5 mL) at room temperature 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 room temperature for 1 h and the layers were separated. The ethereal layer was washed with saturated aqueous NaHCO3 and H2O, dried over MgSO4, filtered and condensed. Flash chromatography (SiO2, 1.5 cm×15 cm, 2% MeOH—CH2Cl2) afforded the title compound (3 mg, 70% yield) as a dark yellow oil: 1H NMR (CDCl3, 250 MHz) δ 9.29 (s, 1H), 5.41-5.27 (m, 2H), 3.10 (t, 2H, J=7.4 Hz), 2.12-1.88 (m, 4H), 1.84-1.75 (m, 2H), 1.47-1.19 (m, 20H), 0.87 (br t, 3H, J=6.6 Hz); IR (CDCl3) νmax 2936, 2855, 1710, 1610, 1562, 1516, 1426, 1372 cm−1; MALDI-FTMS (DHB) m/z 351.2464 ([M+H]+, C20H34N2OS requires 351.2470).

Workup

  1. customthe layers were separated
  2. washThe ethereal layer was washed with saturated aqueous NaHCO3 and H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customcondensed

Sources & evidence

ORD record
ord-3016651e9cad4806b08d284ff43c87bc
Source dataset
uspto-grants-2015_03
Patent number
US08987312B2

Reaction notes

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