Triethylamine → HCID 53649700, compound

HRID 1421078Notes

Reaction equation

HRID 1421078 reaction equation
O[CH2:2][C@H:3]([CH3:24])[CH2:4][O:5][C:6]1[C:7](=[O:23])[O:8][C:9]([CH3:22])([CH3:21])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1.CCN(CC)CC.CS(Cl)(=O)=O.C([O-])(O)=O.[Na+].S([O-])(=O)(=O)C.[F-:47].C([N+](CCCC)(CCCC)CCCC)CCC>C(Cl)Cl.C1COCC1>[F:47][CH2:2][C@H:3]([CH3:24])[CH2:4][O:5][C:6]1[C:7](=[O:23])[O:8][C:9]([CH3:22])([CH3:21])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 21969078HCID 21969078, compound

Product 1

HCID 53649700HCID 53649700, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the alcohol of Example 8 Step 3 (800 mg, 2.25 mmol) in CH2Cl2 (10 mL) at -20∞C. were added Et3N (943 mL, 6.05 mmol) and MsCl (348 mL, 4.51 mmol). After a period of 1 h at 0∞C., saturated NaHCO3 was added. The organic phase was separated, dried over Na2SO4, filtered and evaporated. To the crude mesylate in THF (10.0 mL) was added a 1M THF solution of tetrabutylammonium fluoride (6.77 mL, 6.77 mmol). After a period of 2 h at 50∞C., the reaction mixture was partitioned between 25% NH4OAc and EtOAc. The organic phase was separated, dried over Na2SO4, filtered and evaporated. The title compound (370 mg) was purified by flash chromatography.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. waitAfter a period of 2 h at 50∞C
  6. custom, the reaction mixture was partitioned between 25% NH4OAc and EtOAc
  7. customThe organic phase was separated
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe title compound (370 mg) was purified by flash chromatography

Sources & evidence

ORD record
ord-5a0723a86be440568b6b103bebf23f82
Source dataset
uspto-grants-2000_06
Patent number
US06071954

Reaction notes

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