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

HRID 567687Notes

Reaction equation

HRID 567687 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. 200 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. 200 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-c26a927983234baab253ca1718706b83
Source dataset
uspto-grants-2001_01
Patent number
US06180611B2

Reaction notes

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