Water → (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxypropanoic acid

HRID 1867674Notes

Reaction equation

HRID 1867674 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([O:15]C)=[O:14])[CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.[OH-].[Li+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([OH:15])=[O:14])[CH2:10][O:11][CH3:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 71742038(R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-methoxypropanoate

Product 1

HCID 27281801(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxypropanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl N-(tert-butoxycarbonyl)-O-methyl-D-serinate (2.0 g, 85.7 mmol) was dissolved in tetrahydrofuran (40 ml) and water (20 ml) and lithium hydroxide mono hydrate (1.8 g, 42.9 mmol) added. The mixture was stirred for 4 hours at room temperature, concentrated under reduced pressure to remove most of the tetrahydrofuran and then acidified by the addition of concentrated hydrochloric acid. The solution was extracted with ethyl acetate (three times). The combined organics were dried (MgSO4), filtered and evaporated under reduced pressure to give N-(tert-butoxycarbonyl)-O-methyl-D-serine (1.9 g, 100%) as a colourless oil; 1H NMR spectrum: (DMSO d6) 1.37 (s, 9H), 3.23 (s, 3H), 3.53 (m, 2H), 4.18 (m, 1H), 6.87 (d, 1H), 12.60 (brs, 1H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove most of the tetrahydrofuran
  3. additionacidified by the addition of concentrated hydrochloric acid
  4. extractionThe solution was extracted with ethyl acetate (three times)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-90b50164703e43cfb1233d39d973295e
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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