Ethyl Acetate → HCID 21963939, compound

HRID 2212365Notes

Reaction equation

HRID 2212365 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])[CH2:16][CH2:15][CH:14]([CH2:17][S:18]([N:21]3[CH2:24][CH:23]([OH:25])[CH2:22]3)(=[O:20])=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)(=O)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:26]3[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=3[F:33])[CH2:12][CH2:13][CH:14]([CH2:17][S:18]([N:21]3[CH2:24][C:23](=[O:25])[CH2:22]3)(=[O:19])=[O:20])[CH2:15][CH2:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 21963917HCID 21963917, compound

Product 1

HCID 21963939HCID 21963939, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[4-(4-chloro-benzenesulfonyl)-4-(2,5-difluoro-phenyl)-cyclohexylmethanesulfonyl]-azetidin-3-ol (Example 30) (143 mg, 0.28 mmol.) in dichloromethane (10 mL) was added Dess-Martin periodinane (230 mg, 0.56 mmol.) and the mixture stirred at ambient temperature for 18 hours. Ethyl acetate (20 mL) was added and the solution washed with 10% sodium thiosulfate solution (20 mL), water (20 mL) and brine (20 mL), dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography on silica, eluting with ethyl acetate:dichloromethane:iso-hexane (1:1:2), to afford the desired product (98 mg).

Workup

  1. washthe solution washed with 10% sodium thiosulfate solution (20 mL), water (20 mL) and brine (20 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto leave a residue which
  5. customwas purified by column chromatography on silica
  6. washeluting with ethyl acetate:dichloromethane:iso-hexane (1:1:2)

Sources & evidence

ORD record
ord-5ce17f1be22a4cb3a160e7032b99e8cc
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

Loading…