Water → HCID 178519044, compound

HRID 413264Notes

Reaction equation

HRID 413264 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. customEvaporate the THF under reduced pressure
  2. additiondilute the residue with water
  3. extractionExtract the aqueous mixture with EtOAc
  4. washwash with brine
  5. dry with materialdry (Na2SO4)
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-7ce8b125a4054d41b00b914f74c37f36
Source dataset
uspto-grants-2003_05
Patent number
US06566367B2

Reaction notes

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