Hydrochloric Acid → N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucine

HRID 1744115Notes

Reaction equation

HRID 1744115 reaction equation
[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([O:16]CC2C=CC(OC)=CC=2)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][N:5]([CH3:7])[CH:6]=1.[Li+].[OH-].Cl>CO>[Br:1][C:2]1[C:3]([NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 691531674-methoxybenzyl N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucinate

Product 1

HCID 69151592N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-methoxybenzyl N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucinate (1.19 g, 2.89 mmol) in MeOH (60 mL) was added dropwise an aqueous LiOH solution (1.0 M, 14.5 mL, 14.5 mmol) and the reaction was stirred for ½ hour. The reaction was acidified (pH=4–5) with aqueous 10% HCl and the product extracted with EtOAc (3×), dried over Na2SO4, concentrated in vacuo and purified by flash chromatography over silica gel (Hex/EtOAc/AcOH, 70/29/1, then 50/49/1) to afford N-(4-bromo-1-methyl-1H-pyrazol-3-yl)leucine.

Workup

  1. extractionthe product extracted with EtOAc (3×)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (Hex/EtOAc/AcOH, 70/29/1

Sources & evidence

ORD record
ord-2471e5518402455f82b6410422f766c9
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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