(Diethylamino)sulfur trifluoride → HCID 15542192, compound

HRID 1421080Notes

Reaction equation

HRID 1421080 reaction equation
O[CH2:2][CH:3]([CH3:23])[O:4][C:5]1[C:6](=[O:22])[O:7][C:8]([CH3:21])([CH3:20])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.CCN(S(F)(F)[F:30])CC>C(Cl)Cl>[F:30][CH2:2][CH:3]([CH3:23])[O:4][C:5]1[C:6](=[O:22])[O:7][C:8]([CH3:21])([CH3:20])[C:9]=1[C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 15542191HCID 15542191, compound

Product 1

HCID 15542192HCID 15542192, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the alcohol of Example 12 Step 2 (300 mg, 0.882 mmol) in CH2Cl2 (10 mL) at 0∞C. was added DAST (142 mL, 1.05 mmol). After a period of 18 h at room temperature and 2 days at reflux, the reaction mixture was partitioned between 25% aqueous NH4OAc and EtOAc. The organic phase was separated, dried over Na2SO4, filtered and evaporated under reduced pressure. The title compound (48 mg) was purified by flash chromatography.

Workup

  1. temperature2 days at reflux
  2. customthe reaction mixture was partitioned between 25% aqueous NH4OAc and EtOAc
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe title compound (48 mg) was purified by flash chromatography

Sources & evidence

ORD record
ord-3530bd9046b5411197e60dbd53b64284
Source dataset
uspto-grants-2000_06
Patent number
US06071954

Reaction notes

Loading…