Lithium Hydroxide → (S)-2-((t-Butoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propanoic acid

HRID 1972340Notes

Reaction equation

HRID 1972340 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([O:19]C)=[O:18])[CH2:10][CH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+]>O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][CH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 29947234methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alaninate

Product 1

HCID 7168106(S)-2-((t-Butoxycarbonyl)amino)-3-(tetrahydro-2H-pyran-4-yl)propanoic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500-mL round-bottomed flask was charged with methyl N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alaninate (8.81 g, 30.7 mmol), 100 mL of THF, 100 mL of water and lithium hydroxide (2.20 g, 92 mmol). After stirring overnight at room temperature, the mixture was concentrated and acidified to pH 3 with concentrated aqueous HCl. The mixture was then extracted with EtOAc, dried (MgSO4), filtered, and concentrated to give N-(tert-butoxycarbonyl)-3-(tetrahydro-2H-pyran-4-yl)-L-alanine (8.00 g) as a white solid.

Workup

  1. concentrationthe mixture was concentrated
  2. extractionThe mixture was then extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d3a7818135f74daaa54d455a12ca3682
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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