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

HRID 1593492Notes

Reaction equation

HRID 1593492 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-0965e92f4a5b478d81e1adf50393a64d
Source dataset
uspto-grants-2007_11
Patent number
US07297706B2

Reaction notes

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