Methyl iodide → 4-[[(1,1-dimethylethoxy)carbonyl]amino]Butanoic acid methyl ester

HRID 1855564Notes

Reaction equation

HRID 1855564 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acid

Product 1

HCID 131123524-[[(1,1-dimethylethoxy)carbonyl]amino]Butanoic acid methyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-(tert-butoxycarbonylamino)butanoic acid (7.0 g, 34.5 mmol) and K2CO3 (9.5 g, 68.9 mmol) in acetone (70 mL) was added MeI (7.5 g, 51.8 mmol) at rt. The reaction solution was stirred at 45° C. for 12 hrs. The mixture was washed with water and saturated sodium chloride, dried over Na2SO4, and concentrated to afford methyl 4-(tert-butoxycarbonylamino)butanoate (6.2 g, 83%) as a yellow oil. ESI-MS (EI+, m/z): 240 [M+Na]+.

Workup

  1. washThe mixture was washed with water and saturated sodium chloride
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e1c9ef9794f94568a1c80be697f05d91
Source dataset
uspto-grants-2015_02
Patent number
US08962844B2

Reaction notes

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