Methyl iodide → (2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acid

HRID 1604218Notes

Reaction equation

HRID 1604218 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:16])([O:6][C:7]([NH:9][C@H:10]([C:13]([OH:15])=[O:14])[CH2:11][OH:12])=[O:8])[CH3:5].I[CH3:18]>CN(C=O)C.Cl>[CH3:5][C:4]([CH3:16])([O:6][C:7]([NH:9][C@H:10]([C:13]([OH:15])=[O:14])[CH2:11][O:12][CH3:18])=[O:8])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 98766N-[tert-butoxycarbonyl]-L-serine

Product 1

HCID 7016354(2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acidYield 70.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (60% dispersion, 4.3 g, 0.107 mol) was added portionwise at 0° C. to a stirred solution of (S)-N-(1,1-dimethylethoxy)carbonylserine (10 g, 48.7 mmol) in anhydrous DMF (250 ml). A solution of iodomethane (6.1 ml, 0.1 mol) in anhydrous DMF (10 ml) was then added dropwise. The mixture was allowed to warm to RT and stirred overnight, then diluted with 1N hydrochloric acid to pH3 and the solution concentrated in vacuo to ca. 100 ml. The mixture was diluted with water (200 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine (100 ml), dried (MgSO4) and evaporated in vacuo to provide the title compound as a yellow oil (7.48 g, 70%)

Workup

  1. concentrationthe solution concentrated in vacuo to ca. 100 ml
  2. additionThe mixture was diluted with water (200 ml)
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washThe combined extracts were washed with brine (100 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5325d981038a450f9996adc7e37a850b
Source dataset
uspto-grants-1999_11
Patent number
US05994312

Reaction notes

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