Diisopropylethylamine → HCID 53247993, compound

HRID 2174449Notes

Reaction equation

HRID 2174449 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 being 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-0ed3a4111c304d75a7d585c16b01f70e
Source dataset
uspto-grants-2015_06
Patent number
US09061995B2

Reaction notes

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