Dimethyl Sulfoxide → HCID 68294584, compound

HRID 2279462Notes

Reaction equation

HRID 2279462 reaction equation
[OH-].[K+].CS(C)=O.[C:7]([O:11][C:12]([NH:14][CH2:15][C@H:16]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([F:28])[CH:22]=1)CC(O)=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].I[CH3:30].C[CH2:32][O:33][C:34]([CH3:36])=[O:35]>>[C:7]([O:11][C:12]([N:14]([CH3:30])[CH2:15][C@H:16]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([F:28])[CH:22]=1)[CH2:36][C:34]([O:33][CH3:32])=[O:35])=[O:13])([CH3:8])([CH3:9])[CH3:10]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 86705479HCID 86705479, compound

Product 1

HCID 68294584HCID 68294584, compoundYield 59.9%

Procedure

Powdered KOH (1525 mg, 27.19 mmol) was added to DMSO (3 mL) and the resulting mixture was stirred for 5 min at RT. To this solution was added 100 (902 mg, 2.719 mmol) followed immediately by iodomethane (1.35 mL, 21.75 mmol). The resulting mixture was stirred at RT for 5 h. The reaction mixture was diluted with EtOAc and washed sequentially with H2O, 2M HCl and brine. The organic layer was dried, filtered, and concentrated. The crude product was purified by SiO2 chromatography eluting with 10:1 DCM/EtOAc. The impure product therefrom was rechromatographed under similar conditions to afford 586 mg (59.90%) of (S)-methyl 4-(tert-butoxycarbonyl(methyl)amino)-3-(4-chloro-3-fluorophenyl)butanoate (102).

Workup

  1. stirringThe resulting mixture was stirred at RT for 5 h
  2. washwashed sequentially with H2O, 2M HCl and brine
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by SiO2 chromatography
  7. washeluting with 10:1 DCM/EtOAc
  8. customThe impure product therefrom was rechromatographed under similar conditions

Sources & evidence

ORD record
ord-c3b2a5f49e0946dfa7e1ff26883cba0c
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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