Isopropanol → HCID 61150716, compound

HRID 2227431Notes

Reaction equation

HRID 2227431 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[C:10]([OH:12])=[O:11].S(Cl)(Cl)=O.[CH:17](O)([CH3:19])[CH3:18]>>[CH:17]([O:11][C:10]([C@@H:2]1[CH2:3][C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1]1)=[O:12])([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 2733920Indoline-2-carboxylic acid, (S)-

Product 1

HCID 61150716HCID 61150716, compoundYield 89%

Procedure

To the solution of (2S)-2,3-dihydroindole-2-carboxylic acid (163 mg, 1.0 mmol) in isopropyl alcohol (40 mL), was added thionyl chloride (0.1 mL) slowly. The reaction mixture was heated at reflux for 4 hr with stirring. After cooling, all volatiles were removed under reduced pressure. To the residue saturated aqueous solution of NaHCO3 (10 mL) was added, which was extracted with ethyl acetate (10 mL×3). The extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to give the desired compound (182 mg, 89%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hr
  3. temperatureAfter cooling
  4. customall volatiles were removed under reduced pressure
  5. additionTo the residue saturated aqueous solution of NaHCO3 (10 mL) was added
  6. extractionwhich was extracted with ethyl acetate (10 mL×3)
  7. dry with materialThe extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-73c05b1b2bef48c39aba511cb499966f
Source dataset
uspto-grants-2002_07
Patent number
US06413983B1

Reaction notes

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