Methyl iodide → HCID 15853247, compound

HRID 1929535Notes

Reaction equation

HRID 1929535 reaction equation
[C:1]([NH:8][C:9]([CH3:14])([C:11]([OH:13])=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CCOC(C)=O>[C:4]([O:3][C:1]([NH:8][C:9]([CH3:14])([C:11]([O:13][CH3:15])=[O:12])[CH3:10])=[O:2])([CH3:6])([CH3:7])[CH3:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 15853247HCID 15853247, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Boc-α-methylalanine in DMF (0.4 M) was added K2CO3 (1 eq) and MeI (1.2 eq). The mixture was stirred at RT for 6 h and then diluted with EtOAc, washed with water and sat. aq. NaHCO3. The organic phase was dried over Na2SO4, filtered and concentrated under vacuum to provide the title compound as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ: 7.20 (1H, br. s), 3.58 (3H, s), 1.40-1.27 (15H, m). MS (ES) C10H19NO4 requires: 217. found: 240 (M+Na)+.

Workup

  1. washwashed with water and sat. aq. NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d42ea11486d449649254da111a73d3e8
Source dataset
uspto-grants-2012_05
Patent number
US08188084B2

Reaction notes

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