Sodium Hydroxide → 4-[4-(4-Carboxy-oxazol-5-yl)-phenyl]-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 2278383Notes

Reaction equation

HRID 2278383 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[O:24][CH:23]=[N:22][C:21]=3[C:25]([O:27]CC)=[O:26])=[CH:16][CH:15]=2)[CH2:10][C:9]1([CH3:31])[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[O:24][CH:23]=[N:22][C:21]=3[C:25]([OH:27])=[O:26])=[CH:18][CH:19]=2)[CH2:10][C:9]1([CH3:31])[CH3:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 89741487HCID 89741487, compound

Product 1

HCID 897392914-[4-(4-Carboxy-oxazol-5-yl)-phenyl]-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl esterYield 133.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[4-(4-ethoxycarbonyl-oxazol-5-yl)-phenyl]-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (2.4 g, 5.6 mmol) in 20 mL THF and 20 mL methanol was added 2N aqueous sodium hydroxide solution (11.2 mL, 22.4 mmol). The mixture was stirred at room temperature for 16 hrs and organic solvent was then removed in vacuo. The remaining aqueous mixture was adjusted to pH 4˜5 by the addition of 1N aqueous hydrogen chloride. The mixture was freeze-dried to yield 3 g of 4-[4-(4-carboxy-oxazol-5-yl)-phenyl]-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester as an off-yellow powder, which was used in the next step directly.

Workup

  1. customorganic solvent was then removed in vacuo
  2. additionThe remaining aqueous mixture was adjusted to pH 4˜5 by the addition of 1N aqueous hydrogen chloride
  3. customThe mixture was freeze-dried

Sources & evidence

ORD record
ord-eafa7347112e4dd88b4614265fd909c1
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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