Hydrochloric Acid → (2R)-3-cyclopentyl-2-({[(phenylmethyl)oxy]amino}methyl)propanoic acid

HRID 1366373Notes

Reaction equation

HRID 1366373 reaction equation
[CH:1]1([CH2:6][C@@H:7]2[CH2:10][N:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:8]2=[O:19])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:20][Li].O.Cl.[OH-].[Na+]>C1COCC1.O>[CH:1]1([CH2:6][C@H:7]([CH2:10][NH:9][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([OH:19])=[O:20])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 168937Lithium hydroxide, monohydrateHCID 53718234(r)-1-(Benzyloxy)-3-(cyclopentylmethyl)azetidin-2-one

Product 1

HCID 21305250(2R)-3-cyclopentyl-2-({[(phenylmethyl)oxy]amino}methyl)propanoic acidYield 106.9%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of (3R)-3-(cyclopentylmethyl)-1-[(phenylmethyl)oxy]-2-azetidinone (20 g, 77.1 mmol) and LiOH.H2O (32.4 g, 0.77 mol) in THF/water (500 mL/170 mL) was stirred at room temperature for 36 h. To the reaction mixture was added 6M HCl (130 mL), and then 1 N NaOH was added until a neutral pH was obtained. The layers were separated, and the aqueous layer was extracted once with EtOAc. The combined organics were dried (MgSO4) and concentrated to provide (2R)-3-cyclopentyl-2-({[(phenylmethyl)oxy]amino}methyl)propanoic acid (22.85 g, >100%) as a clear, colorless oil. LCMS: (M+H)+: 277.9.

Workup

  1. customwas obtained
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted once with EtOAc
  4. dry with materialThe combined organics were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9c79064382ef4025807b82981791fb6b
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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