Water → HCID 178519044, compound

HRID 496282Notes

Reaction equation

HRID 496282 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][NH:13][C:14]([N:16]2[CH2:21][CH2:20][C:19]3([C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23](=[O:30])[O:22]3)[CH2:18][CH2:17]2)=[O:15])[CH2:8][CH2:7]1)=[O:5])C.O.O[Li].O>C1COCC1>[C:4]([C@H:6]1[CH2:7][CH2:8][C@H:9]([CH2:12][NH:13][C:14]([N:16]2[CH2:17][CH2:18][C:19]3([C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23](=[O:30])[O:22]3)[CH2:20][CH2:21]2)=[O:15])[CH2:10][CH2:11]1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 178472366HCID 178472366, compound

Product 1

HCID 178519044HCID 178519044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve. 1′-(trans-4-ethoxycarbonyl-cyclohexylmethyl)carbamoyl-spiro[isobenzofuran-1,4′piperidin]-3-one (21 mg, 0.05 mmol) in THF (2 mL) and add an equal volume of water. Add LiOH·H2O (11 mg, 0.26 mmol) to this mixture and heat at 60° C. for 3 hours with stirring. Evaporate the THF under reduced pressure, dilute the residue with water and acidify with 3N HCL. Extract the aqueous mixture with EtOAc, wash with brine, dry (Na2SO4) and concentrate under reduced pressure to obtain 1′-(trans-4-carboxy-cyclohexylmethyl)carbamoyl-spiro[isobenzofuran-1,4′piperidin]-3-one as a white solid.

Workup

  1. dissolutionDissolve
  2. customEvaporate the THF under reduced pressure
  3. additiondilute the residue with water
  4. extractionExtract the aqueous mixture with EtOAc
  5. washwash with brine
  6. dry with materialdry (Na2SO4)
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-95488784b27e48e7a7c7080e79e8aa8e
Source dataset
uspto-grants-2005_09
Patent number
US06943199B2

Reaction notes

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