Hydrochloric Acid → (R)-2-Ethyl-piperazine-1-carboxylic acid 2,6-difluoro-3-methyl-benzyl ester

HRID 1794139Notes

Reaction equation

HRID 1794139 reaction equation
[F:1][C:2]1[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]([F:28])[C:3]=1[CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][C@H:9]1[CH2:21][CH3:22])=[O:7].Cl.O.[OH-].[Na+]>CO.O1CCOCC1>[F:1][C:2]1[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]([F:28])[C:3]=1[CH2:4][O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:21][CH3:22])=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 69141585(R)-2-Ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(2,6-difluoro-3-methyl-benzyl) ester

Product 1

HCID 69141432(R)-2-Ethyl-piperazine-1-carboxylic acid 2,6-difluoro-3-methyl-benzyl esterYield 100.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(R)-2-Ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(2,6-difluoro-3-methyl-benzyl) ester (160 mg) was dissolved in methanol (3 mL), 500 μL 4 N HCl in dioxane was added and the mixture was stirred for 18 h at room temperature. The mixture was added to water (10 mL) made alkaline with 1 N NaOH and extracted with ethylacetate. Organic phases were pooled, dried with Na2SO4 and evaporated to give the product as a yellowish oil (120 mg); MS (ISP): 299.4 (M+H)+.

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialdried with Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-120c65ce39f843969072380da9914de4
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…