Lithium hydroxide, monohydrate → (2R)-2-({[(Phenylmethyl)oxy]amino}methyl)hexanoic acid

HRID 1396862Notes

Reaction equation

HRID 1396862 reaction equation
[CH2:1]([C@@H:5]1[CH2:8][N:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].[OH2:18].[OH-].[Li+]>C1COCC1.CO.O>[C:11]1([CH2:10][O:9][NH:7][CH2:8][C@@H:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([OH:17])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 16037946(3R)-1-(Benzyloxy)-3-butylazetidin-2-one

Product 1

HCID 11694494(2R)-2-({[(Phenylmethyl)oxy]amino}methyl)hexanoic acidYield 69.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (3R)-3-butyl-1-[(phenylmethyl)oxy]-2-azetidinone (7) (52.8 g, 0.23 mol) in THF/MeOH (3:1, 1500 mL) at 0° C. was added Lithium hydroxide monohydrate (11.4 g, 0.27 mol) in water (375 mL). The mixture was warmed up to rt and stirred overnight. TLC indicated completion of the reaction. Organic solvents were removed under vacuum, and the aqueous solution was washed with DCM, acidified with 4 N HCl to pH ˜2.0, and extracted with DCM. The extracts were dried, filtered and concentrated to provide the title compound (40 g, 69%). LCMS: (M+H)+: 252.2.

Workup

  1. customcompletion of the reaction
  2. customOrganic solvents were removed under vacuum
  3. washthe aqueous solution was washed with DCM
  4. extractionextracted with DCM
  5. customThe extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bdae07fc8e4c490590daac1574a3370c
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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