Hydrochloric Acid → 2-(4-(4-(4-(1,1-Dimethylethoxycarbonyl)piperazin-1-yl)phenylcarbonylamino)-3-methylphenoxy)acetic acid

HRID 1459414Notes

Reaction equation

HRID 1459414 reaction equation
[CH3:1][C:2]([CH3:36])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([NH:21][C:22]3[CH:34]=[CH:33][C:25]([O:26][CH2:27][C:28]([O:30]CC)=[O:29])=[CH:24][C:23]=3[CH3:35])=[O:20])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:3].CO.[OH-].[Na+].Cl>O>[CH3:3][C:2]([CH3:36])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([NH:21][C:22]3[CH:34]=[CH:33][C:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:24][C:23]=3[CH3:35])=[O:20])=[CH:17][CH:18]=2)[CH2:9][CH2:8]1)=[O:6])[CH3:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 54494373Ethyl 2-(4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylcarbonylamino)-3-methylphenoxy)acetate

Product 1

HCID 541756292-(4-(4-(4-(1,1-Dimethylethoxycarbonyl)piperazin-1-yl)phenylcarbonylamino)-3-methylphenoxy)acetic acidYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round bottomed flask with a stirring bar and an argon inlet was added ethyl 2-(4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylcarbonylamino)-3-methylphenoxy)acetate (1.22 g, 2.45 mmol) and 20 mL of CH3OH. To this solution was added aqueous NaOH (10 mL of a 1N solution). The mixture was stirred at ambient temperature for 18 h. The mixture was neutralized with 10 mL of 1N HCl and diluted with H2O. The product was collected on a frit and washed with a little H2O. This material was dried in vacuo to give 0.953 g (83%) of 2-(4-(4-(4-(1,1-dimethylethoxycarbonyl)piperazin-1-yl)phenylcarbonylamino)-3-methylphenoxy)acetic acid as a white solid.

Workup

  1. customThe product was collected on a frit
  2. washwashed with a little H2O
  3. customThis material was dried in vacuo

Sources & evidence

ORD record
ord-93a697d17ca64ccfb0d6719d3a337e85
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

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