Methanesulfinic acid → HCID 58573831, compound

HRID 932258Notes

Reaction equation

HRID 932258 reaction equation
[CH3:1][S:2]([O-:5])(=O)=[O:3].[CH2:6]([C@@:9]1([CH3:35])[CH2:14][C@H:13]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)[C@@H:12]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[N+:11]2[C@@H:30]([CH2:33][CH3:34])[CH2:31][O:32][C:10]1=2)[CH:7]=[CH2:8].CS(O)=O.[Na]>CC#N>[CH2:6]([C@@:9]1([CH3:35])[CH2:14][C@H:13]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)[C@@H:12]([C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[N:11]([C@@H:30]([CH2:33][CH3:34])[CH2:31][S:2]([CH3:1])(=[O:5])=[O:3])[C:10]1=[O:32])[CH:7]=[CH2:8]

Participants

5

Reactant 3

HCID 87251Methanesulfinic acidHCID 5360545SodiumHCID 86660748HCID 86660748, compound

Product 1

HCID 58573831HCID 58573831, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
114 °C

Procedure

To a solution of (3S,5S,6R,8S)-8-allyl-6-(3-chloro-5-fluorophenyl)-5-(4-chlorophenyl)-3-ethyl-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium methanesulfonate (Example 395, step A, 100 mg, 0.184 mmol) in MeCN (1.8 mL) was added methanesulfinic acid, sodium salt (56.5 mg, 0.553 mmol). The mixture was heated to 114° C. After heating for 24 hours, the mixture was cooled to room temperature and stirred for 2 days. The mixture was partitioned between EtOAc and aq. NH4Cl. The organic layer was washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (eluent: 20 to 60% EtOAc/hexanes, gradient elution) to afford the title compound.

Workup

  1. temperatureAfter heating for 24 hours
  2. temperaturethe mixture was cooled to room temperature
  3. customThe mixture was partitioned between EtOAc and aq. NH4Cl
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by flash chromatography on silica gel (eluent: 20 to 60% EtOAc/hexanes, gradient elution)

Sources & evidence

ORD record
ord-56ace071a14a47a69c689c44d351b0dc
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

Loading…