Methyl bromoacetate → N-Boc-allylglycine methyl ester

HRID 1466014Notes

Reaction equation

HRID 1466014 reaction equation
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].[Li+].CC([N-]C(C)C)C.Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>C1COCC1>[CH2:1]([N:4]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:5]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:11])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 4067274tert-butyl N-(prop-2-en-1-yl)carbamate

Product 1

HCID 22243128N-Boc-allylglycine methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-Butyl allylcarbamate (7.2 g, 46 mmol) in THF at −78° C. was added LDA (31 mL, 1.5 M in cyclohexane) by syringe. The reaction was allowed to stir for 10 minutes before methyl bromoacetate (7.0 g, 46 mmol) was added. The reaction was then allowed to warm to RT. The reaction was quenched with water, extracted with EtOAc, dried over magnesium sulfate, and purified by silica gel chromatography (with 15% EtOAc-Hexanes). Removal of solvents provided the title compound. LC-MS (IE, m/z): 130 [M−Boc+1]+.

Workup

  1. additionwas added
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialdried over magnesium sulfate
  5. custompurified by silica gel chromatography (with 15% EtOAc-Hexanes)
  6. customRemoval of solvents

Sources & evidence

ORD record
ord-37b04dd04f5d4945af3def3da232b252
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

Loading…