(Diethylamino)sulfur trifluoride → HCID 67982275, compound

HRID 595373Notes

Reaction equation

HRID 595373 reaction equation
[C:1]([O:9][CH2:10][C@H:11]1[O:19][C@H:18]2[C@H:14]([N:15]=[C:16]([N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH3:22])[S:17]2)[C@@H:13](O)[C@@H:12]1[O:31][C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(S(F)(F)[F:46])CC>C(Cl)Cl>[C:1]([O:9][CH2:10][C@H:11]1[O:19][C@H:18]2[C@H:14]([N:15]=[C:16]([N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH3:22])[S:17]2)[C@@H:13]([F:46])[C@@H:12]1[O:31][C:32](=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 67983005HCID 67983005, compound

Product 1

HCID 67982275HCID 67982275, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (-(3aR,5R,6S,7R,7aR)-6-(benzoyloxy)-2-((tert-butoxycarbonyl)(ethyl)amino)-7-hydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methyl benzoate (0.49 g, 0.88 mmol) in anhydrous DCM (3 mL), at −40° C. under N2, was added DAST (1.0 g, 6.2 mmol). After addition the mixture was stirred at room temperature overnight. After the reaction mixture was again cooled at −40° C., it was diluted with DCM (20 mL), and then quenched by adding satd. aqueous NaHCO3 dropwise. The organic layer was collected, and the aqueous was extracted with DCM (2×15 mL). The combined extract was dried over anhydrous Na2SO4. After filtration the solvent was evaporated under reduced pressure, and the residue was purified on silica gel by flash column chromatography (EtOAc/hexanes, 1:5 to 2:7), affording (-(3aR,5R,6R,7R,7aR)-6-(benzoyloxy)-2-((tert-butoxycarbonyl)(ethyl)amino)-7-fluoro-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)methyl benzoate as a white solid (0.14 g, impure, ˜28%).

Workup

  1. additionAfter addition the mixture
  2. temperatureAfter the reaction mixture was again cooled at −40° C.
  3. customquenched
  4. additionby adding satd
  5. customThe organic layer was collected
  6. extractionthe aqueous was extracted with DCM (2×15 mL)
  7. extractionThe combined extract
  8. dry with materialwas dried over anhydrous Na2SO4
  9. filtrationAfter filtration the solvent
  10. customwas evaporated under reduced pressure
  11. customthe residue was purified on silica gel by flash column chromatography (EtOAc/hexanes, 1:5 to 2:7)

Sources & evidence

ORD record
ord-2a7e724e1424412fb97c5c3068959dc9
Source dataset
uspto-grants-2016_01
Patent number
US09243020B2

Reaction notes

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