Hydrochloric Acid → (R)-2-Ethyl-piperazine-1-carboxylic acid 4-cyclopropylmethoxy-2,6-difluoro-benzyl ester

HRID 1794143Notes

Reaction equation

HRID 1794143 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:30]=[C:29]([F:31])[C:9]([CH2:10][O:11][C:12]([N:14]3[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C@H:15]3[CH2:27][CH3:28])=[O:13])=[C:8]([F:32])[CH:7]=2)[CH2:3][CH2:2]1.Cl.[OH-].[Na+]>CO.O1CCOCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:30]=[C:29]([F:31])[C:9]([CH2:10][O:11][C:12]([N:14]3[CH2:19][CH2:18][NH:17][CH2:16][C@H:15]3[CH2:27][CH3:28])=[O:13])=[C:8]([F:32])[CH:7]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69194614(R)-2-Ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(4-cyclopropylmethoxy-2,6-difluoro-benzyl)ester

Product 1

HCID 66838349(R)-2-Ethyl-piperazine-1-carboxylic acid 4-cyclopropylmethoxy-2,6-difluoro-benzyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(R)-2-Ethyl-piperazine-1,4-dicarboxylic acid 4-tert-butyl ester 1-(4-cyclopropylmethoxy-2,6-difluoro-benzyl) ester (400 mg) was dissolved in methanol (5 mL), 1100 μL 4 N HCl in dioxane was added and the mixture was stirred for 18 h at room temperature. The mixture was made alkaline with 2 N NaOH and eluted with ethylacetate over a column containing 10 g ChemElut CE1010. The filtrate was collected, solvent was evaporated to give a yellowish oil (237 mg). This residue was purified by column chromatography (silica gel; dichloromethane/methanol gradient) to yield 186 mg (59%) of the product as a colorless oil. MS (ISP): 355.4 (M+H)+.

Workup

  1. washeluted with ethylacetate over a column
  2. additioncontaining 10 g ChemElut CE1010
  3. customThe filtrate was collected
  4. customsolvent was evaporated

Sources & evidence

ORD record
ord-f35729cef42f48eca202847108df54af
Source dataset
uspto-grants-2006_04
Patent number
US07022707B2

Reaction notes

Loading…