Hydrochloric Acid → HCID 59474985, compound

HRID 42538Notes

Reaction equation

HRID 42538 reaction equation
[C:1]([NH:9][C@@H:10]1[CH2:19][CH2:18][C:13]2(OCC[O:14]2)[CH2:12][C@@H:11]1[C:20]([OH:22])=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(#N)C>[C:1]([NH:9][C@@H:10]1[CH2:19][CH2:18][C:13](=[O:14])[CH2:12][C@@H:11]1[C:20]([OH:22])=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59474978HCID 59474978, compound

Product 1

HCID 59474985HCID 59474985, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(7S,8R)-8-Benzamido-1,4-dioxaspiro[4.5]decane-7-carboxylic acid (750 mg, 2.456 mmol) was dissolved in acetonitrile (10 mL) at 25° C. with stirring. 1N HCl (12.28 mL, 12.28 mmol) was then added thereto and the reaction stirred at 25° C. for about 16 hours. The reaction was concentrated to remove the acetonitrile. White solids precipitated and ethyl acetate and THF were added to dissolve the solids. The resulting mixture was rinsed (3×) with water. The organic layer was dried over sodium sulfate and concentrated to give (1S,2R)-2-benzamido-5-oxocyclohexanecarboxylic acid (430 mg, 1.646 mmol, 67.0% yield) as a white solid. MS (ESI+)=262.11 (M+H)+.

Workup

  1. stirringthe reaction stirred at 25° C. for about 16 hours
  2. concentrationThe reaction was concentrated
  3. customto remove the acetonitrile
  4. customWhite solids precipitated
  5. additionethyl acetate and THF were added
  6. dissolutionto dissolve the solids
  7. washThe resulting mixture was rinsed (3×) with water
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-04836653a0684da5866de2bb723884f2
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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