Water → 3-{[(tert-Butoxycarbonyl)(butyl)amino]methyl}-5-methylbenzoic Acid

HRID 14144Notes

Reaction equation

HRID 14144 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:17]([O:19]C)=[O:18])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>CO.O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:17]([OH:19])=[O:18])[CH2:9][CH2:10][CH2:11][CH3:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 21086193HCID 21086193, compound

Product 1

HCID 210858673-{[(tert-Butoxycarbonyl)(butyl)amino]methyl}-5-methylbenzoic Acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 3-{[(tert -butoxycarbonyl)(butyl)amino]methyl}-5-methylbenzoate (70 mg, 0.21 mmol) in methanol (2 mL), tetrahydrofuran (1 mL), and water (1 mL) is added lithium hydroxide (88 mg, 2.1 mmol), and the reaction mixture stirred at room temperature for 2 h. The reaction mixture is concentrated under reduced pressure, dissolved in methylene chloride, filtered, and the filtrate concentrated under reduced pressure to provide the title compound.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. dissolutiondissolved in methylene chloride
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-e75fcc1cc8834dd5a9f293fa26fd6f2f
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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