Hydrochloric Acid → HCID 86703769, compound

HRID 1849889Notes

Reaction equation

HRID 1849889 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:36])[CH2:21][C:22]2[C:31]([CH:32]3[CH2:34][CH2:33]3)=[CH:30][C:25]([C:26]([O:28]C)=[O:27])=[C:24]([F:35])[CH:23]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1.CO.[OH-].[Li+]>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([C:20](=[O:36])[CH2:21][C:22]2[C:31]([CH:32]3[CH2:34][CH2:33]3)=[CH:30][C:25]([C:26]([OH:28])=[O:27])=[C:24]([F:35])[CH:23]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86703768HCID 86703768, compound

Product 1

HCID 86703769HCID 86703769, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(2-(4-benzhydrylpiperazin-1-yl)-2-oxoethyl)-5-cyclopropyl-2-fluorobenzoate (70 mg, 0.14 mmol) in THF (2 mL) and methanol (2 mL), lithium hydroxide (2M, 2 mL) was added. After stirring at room temperature for 16 h, the mixture pH was adjusted to 2-3 with HCl (2 M) and extracted by ethyl acetate (10 mL×3). The combined organic layers were washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Combiflash (30%-40% CH3CN in 0.1% HCOOH) to afford target compound (35 mg, 53%) as a white solid. LCMS (ESI): m/z: 473.2 [M+H]+.

Workup

  1. extractionextracted by ethyl acetate (10 mL×3)
  2. washThe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by Combiflash (30%-40% CH3CN in 0.1% HCOOH)

Sources & evidence

ORD record
ord-a4d944d058194b95b6f474c5558e763e
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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