Potassium Carbonate → HCID 23138701, compound

HRID 1171689Notes

Reaction equation

HRID 1171689 reaction equation
C(=O)([O-])[O-].[K+].[K+].[ClH:7].C([S:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[C:19]([CH:21]2[CH2:23][CH2:22]2)=[O:20])[CH2:14]/[C:13]/1=[CH:31]\[C:32]1[N:36]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[N:35]=[N:34][N:33]=1)(=O)C>CO>[ClH:7].[CH:21]1([C:19](=[O:20])[CH:18]([N:15]2[CH2:16][CH2:17][CH:12]([SH:11])/[C:13](=[CH:31]/[C:32]3[N:36]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[N:35]=[N:34][N:33]=3)/[CH2:14]2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86609438HCID 86609438, compound

Product 1

HCID 23138701HCID 23138701, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (74 mg) was added to a solution of (E)-4-(acetylsulfanyl)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-{[1-(methoxycarbonylmethyl)-1H-tetrazol-5-yl]methylidene}piperidine hydrochloride (128 mg) in methanol (5 ml). After being stirred at room temperature for 15 minutes, the mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave a residue, which was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.024N hydrochloric acid, 30/70, v/v) to give (E)-1-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-3-{[1-(methoxycarbonylmethyl)-1H-tetrazol-5-yl]methylidene}-4-sulfanylpiperidine hydrochloride (57 mg, gross yield: 49%, a part of this product had been hydrolyzed at the methyl ester moiety). This product (40 mg) was treated with hydrochloric acid in a similar manner to that described in Example 134, and the resulting product was purified by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/0.024 N hydrochloric acid, 25/75, v/v) to afford the title compound (13 mg, yield: 34%) as a colourless amorphous solid.

Workup

  1. customthe mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationConcentration under reduced pressure
  6. customgave a residue, which
  7. customwas purified by preparative HPLC (YMC-Pack ODS-A

Sources & evidence

ORD record
ord-a3ada30b5a624bf5a1fa9a11dc848dd9
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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