Hydrochloric Acid → HCID 58324399, compound

HRID 69719Notes

Reaction equation

HRID 69719 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[CH:7][C:6]([N:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[C:5]([F:23])[CH:4]=1)#N.[OH-:24].[Na+].Cl.[OH2:27]>C(O)C>[C:19]([O:18][C:16]([N:13]1[CH2:14][CH2:15][N:10]([C:6]2[C:5]([F:23])=[CH:4][C:3]([C:1]([OH:27])=[O:24])=[C:8]([F:9])[CH:7]=2)[CH2:11][CH2:12]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 58324419HCID 58324419, compound

Product 1

HCID 58324399HCID 58324399, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Tert-butyl 4-(4-cyano-2,5-difluorophenyl)piperazine-1-carboxylate (20 mg, 0.062 mmol) was dissolved in ethanol (1 mL) and treated with water (0.2 mL) and 50% NaOH (0.2 mL, 2.500 mmol). The reaction mixture was stirred at 90° C. for 1 h, diluted with water (2 mL) and acidified with 1N HCl to pH<4. The solid was filtered, washed with water and dried in vacuum to afford 4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-2,5-difluorobenzoic acid (21.0 mg, 0.061 mmol, 99% yield) as a white solid. ESI-MS: m/z 343 (M+H)+.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water
  3. customdried in vacuum

Sources & evidence

ORD record
ord-9ef1577c58434c5b954f71f3b031cea3
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Reaction notes

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