Diisopropylethylamine → HCID 53247993, compound

HRID 1914438Notes

Reaction equation

HRID 1914438 reaction equation
Br[CH2:2][CH2:3][CH:4]([S:9]([OH:12])(=[O:11])=[O:10])[C:5]([O:7][CH3:8])=[O:6].[C:13]([OH:16])(=[S:15])[CH3:14].CCN(C(C)C)C(C)C>C1COCC1>[C:13]([S:15][CH2:2][CH2:3][CH:4]([S:9]([OH:12])(=[O:11])=[O:10])[C:5]([O:7][CH3:8])=[O:6])(=[O:16])[CH3:14]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 53247992HCID 53247992, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 53247993HCID 53247993, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

5.0 g (19.2 mmol) of 4-bromo-1-methoxy-1-oxobutane-2-sulfonic acid in 100 ml of THF was added 3.0 ml of thioacetic acid and 9.0 ml of DIPEA in 100 ml of THF. The mixture was stirred overnight then refluxed at 70° C. for 1 hr, evaporated and co-evaporated with 3×100 ml of water after neutralized to pH 7 with NaHCO3. The mixture was redissolved in methanol, filtered through celite, concentrated and purified with SiO2 chromatography eluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1) to afford 4.4 g (90% yield) of the title compound. 1H NMR (D2O) 3.95 (dd, 1H, J=4.1, 10.3 Hz), 3.83 (s, 3H), 3.74 (m, 2H), 3.22 (dd, 2H, J=7.4, 14.9 Hz), 2.39 (s, 3H); 13C NMR 203.88, 172.91, 67.32, 56.17, 29.04, 20.61; MS m/z− 254.8 (M−H)

Workup

  1. customevaporated
  2. dissolutionThe mixture was redissolved in methanol
  3. filtrationfiltered through celite,
  4. concentrationconcentrated
  5. custompurified with SiO2 chromatography
  6. washeluted with CH3OH/CH2Cl2/HCOOH 37.5:250:1 to 50:250:1)

Sources & evidence

ORD record
ord-3ef96d7982f146d6a8624e12254c6632
Source dataset
uspto-grants-2013_12
Patent number
US08613930B2

Reaction notes

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