Sodium Hydroxide → 6-(4-(Tert-butoxycarbonyl)piperazin-1-yl)quinoxaline-2-carboxylic acid

HRID 509091Notes

Reaction equation

HRID 509091 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([C:24]([O:26]CC)=[O:25])[CH:18]=[N:17]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CCO.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[C:19]([C:24]([OH:26])=[O:25])[CH:18]=[N:17]3)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86731466Ethyl 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)quinoxaline-2-carboxylate

Product 1

HCID 867314676-(4-(Tert-butoxycarbonyl)piperazin-1-yl)quinoxaline-2-carboxylic acidYield 56%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of ethyl 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)quinoxaline-2-carboxylate (500 mg, 1.3 mmol) in EtOH/THF (5 mL) was added NaOH (5 ml, 2 mmol) followed by stirring for 2 hrs at r.t. After extraction by EA, the combined organic layers were concentrated in vacuo to yield 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)quinoxaline-2-carboxylic acid as a red solid (260 mg, yield: 56%).

Workup

  1. extractionAfter extraction by EA
  2. concentrationthe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-7b11e3ee00684471b064494369109763
Source dataset
uspto-grants-2015_08
Patent number
US09096549B2

Reaction notes

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