Methanol → HCID 58303877, compound

HRID 1404126Notes

Reaction equation

HRID 1404126 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([F:18])[C:5]([O:15][CH2:16][CH3:17])=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][C:12]([OH:14])=[O:13].O=S(Cl)Cl.[CH3:23]O>>[Cl:1][C:2]1[CH:3]=[C:4]([F:18])[C:5]([O:15][CH2:16][CH3:17])=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH2:11][C:12]([O:14][CH3:23])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 66927233HCID 66927233, compound

Product 1

HCID 58303877HCID 58303877, compoundYield 82%

Procedure

To a solution of 30-9 (582 mg, 6.4 mmol) in CH3OH (20 mL) was added SOCl2 (1 mL). The mixture was refluxed for 2 h before it was cooled to room temperature, the solvent was removed under reduce pressure. The resulting residue was partitioned between water (30 mL) and ethyl acetate (30 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were combined, washed with brine (3×20 mL), dried over Na2SO4, filtered and concentrated to afford 30-10 (500 mg, 82%) as a light yellow solid. LRMS: calc 285.0 and found: 286.1 [M+1].

Workup

  1. temperatureThe mixture was refluxed for 2 h before it
  2. customthe solvent was removed
  3. customThe resulting residue was partitioned between water (30 mL) and ethyl acetate (30 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (3×20 mL)
  6. washwashed with brine (3×20 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a32c0d7d35854549a0d642f2352d64d7
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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