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

HRID 1641352Notes

Reaction equation

HRID 1641352 reaction equation
[H-].[Na+].[C:3]([NH:10][C@H:11]([C:14]([OH:16])=[O:15])[CH2:12][OH:13])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[O-][CH2:18]C.[Na+].CI>C1COCC1.CO>[C:6]([O:5][C:3]([NH:10][C@@H:11]([CH2:12][O:13][CH3:18])[C:14]([OH:16])=[O:15])=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 2723922Sodium ethoxide2×

Product 1

HCID 7016354(2S)-2-(((tert-butoxy)carbonyl)amino)-3-methoxypropanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Under nitrogen a mixture of 74 ml abs. THF and 6 ml abs. methanol is cooled to −70° C. and 2 g sodium hydride (55-65% dispersion) are added. The suspension is stirred for 0.4 hour at ambient temperature. Under nitrogen, 2.05 g N-Boc-L-serine are suspended in 100 ml abs. THF and 40 ml of the prepared sodium ethoxide solution are added. The suspension is stirred for 1 hour at ambient temperature and 1 ml methyliodide are added. After 1 hour the remainder of the sodium ethoxide solution and another 2 ml of methyliodide are added. After 18 hours the reaction mixture is evaporated to dryness. The residue is washed with water and ether and extracted. The water phase is acidified and extracted with ethyl acetate and dichloromethane. 0.52 g of the product are obtained.

Workup

  1. additionUnder nitrogen a mixture of 74 ml abs
  2. stirringThe suspension is stirred for 1 hour at ambient temperature
  3. customAfter 18 hours the reaction mixture is evaporated to dryness
  4. washThe residue is washed with water and ether
  5. extractionextracted
  6. extractionextracted with ethyl acetate and dichloromethane

Sources & evidence

ORD record
ord-53d40c4e2ac64718bbb2f2a2d475f00f
Source dataset
uspto-grants-2012_02
Patent number
US08114878B2

Reaction notes

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