Lithium Hydroxide → (2R,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxybutanoic acid

HRID 1792778Notes

Reaction equation

HRID 1792778 reaction equation
C[O:2][C:3](=[O:17])[C@@H:4]([C@H:13]([CH3:16])[O:14][CH3:15])[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[Li+].[OH-]>O1CCOCC1.O>[C:6]([NH:5][C@@H:4]([C:3]([OH:17])=[O:2])[C@H:13]([CH3:16])[O:14][CH3:15])([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 23540192HCID 23540192, compound

Product 1

HCID 23540191(2R,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-methoxybutanoic acidYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-Boc-O-methyl-D-threonine methyl ester (8.09 mmol) in 1,4-dioxane (10 mL) is added a solution of LiOH (24.3 mmol) in water (20 mL). After stirring for 2–3 h, the solvents are removed in vacuo and the residue partitioned between water and ether. The aqueous layer is acidified with solid citric acid to approximately pH 3, then extracted with ethyl acetate. The ethyl acetate extract is washed with water, dried with MgSO4, filtered and concentrated in vacuo to yield 1.70 g (90%) of the title compound.

Workup

  1. customthe solvents are removed in vacuo
  2. customthe residue partitioned between water and ether
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washis washed with water
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbaa94bd32244bae89e10ca244ba911a
Source dataset
uspto-grants-2006_07
Patent number
US07078415B2

Reaction notes

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