2,6-Lutidine → HCID 86726818, compound

HRID 1499601Notes

Reaction equation

HRID 1499601 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:35])[C@H:15]([CH:32]1[CH2:34][CH2:33]1)[C@H:16]([C@H:18]1[CH2:22][O:21][C:20]([CH3:24])([CH3:23])[N:19]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])(=O)=O>C(Cl)Cl.ClCCCl>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:35])[C@H:15]([CH:32]1[CH2:33][CH2:34]1)[C@H:16]([C@H:18]1[CH2:22][O:21][C:20]([CH3:23])([CH3:24])[N:19]1[C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[O:17][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 86726816HCID 86726816, compound

Product 1

HCID 86726818HCID 86726818, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a −40° C. solution of tert-butyl (4R)-4-{(1R,2R)-3-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-cyclopropyl-1-hydroxy-3-oxopropyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (1.80 g, 3.68 mmol) in anhydrous DCM (10 mL), 2,6-lutidine (0.85 mL, 7.3 mmol) was added under an atmosphere of nitrogen. After 10 min., a solution of tert-butyldimethylsilyl trifluoromethanesulfonate (1.1 mL, 4.9 mmol) in anhydrous DCM (1 mL) was added. The reaction mixture was allowed to warm gradually to ambient temperature while stirring overnight. The crude reaction mixture was diluted with 1,2-dichloroethane and cooled to 0° C. prior to quenching with saturated NaHCO3 (aq.). Upon separation of the two layers that resulted, the organic layer was washed with water and brine, dried over Na2SO4, concentrated under reduced pressure and purified by flash chromatography (120 g silica gel, eluting with 0-30% EtOAc/hexanes) to afford the sub-title compound (2.1 g, 95%). LC/MS (ESI) m/z calc. for C32H50N2O7SiNa: 625.3 [M+Na]+. found 625.1.

Workup

  1. customThe crude reaction mixture
  2. temperaturecooled to 0° C.
  3. customto quenching with saturated NaHCO3 (aq.)
  4. customUpon separation of the two layers
  5. customthat resulted
  6. washthe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. custompurified by flash chromatography (120 g silica gel, eluting with 0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d524d981780f4ed29a62e435889ce75e
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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