Hydrochloric Acid → HCID 59202200, compound

HRID 1685812Notes

Reaction equation

HRID 1685812 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][S:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.Cl.C([BH3-])#N.[Na+]>CO>[OH:1][CH:2]1[CH2:6][CH2:5][S:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 59202233HCID 59202233, compound

Product 1

HCID 59202200HCID 59202200, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[4-(3-Oxothiolan-2-ylmethyl)phenyl]propionic acid (100 mg) obtained in Example 26 was dissolved in methanol (3.0 ml), and to the solution was added concentrated hydrochloric acid (0.3 ml), and then sodium cyanoborohydride (50 mg) was added. The mixture was stirred overnight, then concentrated under reduced pressure, and extracted with ethyl acetate, and the organic layer was concentrated under reduced pressure. The resulting residue was dissolved in methanol (3.0 ml), and to the solution was added aqueous lithium hydroxide monohydrate (16 mg, 2.0 ml). The mixture was stirred for 30 minutes, then concentrated under reduced pressure, then the residue was acidified with diluted hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, then dried over magnesium sulfate, and concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give isomers of the title compound, compounds of Example 27-A (colorless crystals, 21 mg, 21%) and Example 27-B (colorless oil, 44 mg, 44%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. dissolutionThe resulting residue was dissolved in methanol (3.0 ml)
  5. additionto the solution was added aqueous lithium hydroxide monohydrate (16 mg, 2.0 ml)
  6. stirringThe mixture was stirred for 30 minutes
  7. concentrationconcentrated under reduced pressure
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-abe168c7304f420cb1d535d0770cacce
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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