18-Crown-6 → (4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-(methylsulfonylmethyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylate

HRID 1500286Notes

Reaction equation

HRID 1500286 reaction equation
[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:18][N:17]=[C:16]([CH2:19]OS(C)(=O)=O)[CH:15]=3)=[CH:10][CH:9]=2)[O:6][C:5]([CH3:26])([CH3:25])[N:4]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[CH3:34][S:35]([O-:37])=[O:36].[Na+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:9]=[CH:10][C:11]([C:14]3[O:18][N:17]=[C:16]([CH2:19][S:35]([CH3:34])(=[O:37])=[O:36])[CH:15]=3)=[CH:12][CH:13]=2)[O:6][C:5]([CH3:25])([CH3:26])[N:4]1[C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 2733271Sodium methanesulfinateHCID 86695496(4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-((methylsulfonyloxy)methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylate

Product 1

HCID 86713172(4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-(methylsulfonylmethyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylateYield 77.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-((methylsulfonyloxy)methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylate (200 mg, 0.413 mmol), sodium methanesulfinate (100 mg, 0.83 mmol), and 18-crown-6 (23 mg, 0.08 mmol) in acetonitrile (8 mL) are stirred at room temperature for 16 hours then the mixture is concentrated and purified by column chromatography on silica gel eluting with a gradient of ethyl acetate/heptane to afford the title compound (150 mg). m/z (Cl) 469 [M+H].

Workup

  1. concentrationthe mixture is concentrated
  2. custompurified by column chromatography on silica gel eluting with a gradient of ethyl acetate/heptane

Sources & evidence

ORD record
ord-71910439d9c0478b85da387d57d73c6b
Source dataset
uspto-grants-2015_12
Patent number
US09206126B2

Reaction notes

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