(R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid → (R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid

HRID 249887Notes

Reaction equation

HRID 249887 reaction equation
[CH2:1]([N:8]([C@H:13]([CH2:17][OH:18])[C:14]([OH:16])=[O:15])[C:9](=[O:12])[CH2:10]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(C)(C)C.[K+]>C(O)(C)(C)C>[CH2:1]([N:8]1[C:9](=[O:12])[CH2:10][O:18][CH2:17][C@@H:13]1[C:14]([OH:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 13543368(R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 13543371(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic AcidYield 59%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (R)-2-(N-benzyl-2-chloroacetamido)-3-hydroxypropanoic acid (1.53 g, 5.63 mmol) in tert-butanol was added potassium tert-butanolate and the reaction mixture heated to 110° C. for three h, then cooled to room temperature and concentrated to dryness. The residue was acidified with 1 N HCl to pH 1 and the aqueous solution extracted with EtOAc (3×250 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10 to 30% CH3OH in CH2Cl2 with 1% acetic acid) to provide (R)-4-benzyl-5-oxomorpholine-3-carboxylic acid (780 mg, 59%) as a yellow foam. 1H NMR and MS consistent.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated to dryness
  3. extractionthe aqueous solution extracted with EtOAc (3×250 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, 10 to 30% CH3OH in CH2Cl2 with 1% acetic acid)

Sources & evidence

ORD record
ord-492b44967f864f49bed5e17b652b7f80
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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