Hydrochloric Acid → (R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid

HRID 421189Notes

Reaction equation

HRID 421189 reaction equation
[C:1]1([CH2:7][NH:8][C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:16][C:17](Cl)=[O:18].Cl>[OH-].[Na+]>[O:18]=[C:17]1[N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@@H:9]([C:12]([OH:14])=[O:13])[CH2:10][O:11][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 13543366(R)-2-(Benzylamino)-3-hydroxypropanoic acid

Product 1

HCID 13543371(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

The title compound was prepared according to the method described by H. H. Otto, Helvetica Chimica Acta, 2004, 87, 90. To an ice cooled solution of N-(phenylmethyl)-D-serine (8.90 g, 45.59 mmol) in 2N NaOH solution (50 mL) was added chloroacetyl chloride (4.36 mL, 54.71 mmol), dropwise over 15 minutes. The reaction was stirred for 30 minutes before adding 30% NaOH solution (4.5 g in 15 mL) and stirring at R.T. for 2 and ½ hours. It was cooled in an ice bath before adding c.HCl solution to pH<1. solid precipitated out. Filtered. Suspended in isopropanol and heated at reflux for 10 minutes. Filtered hot. Solvent evaporated to afford a pale yellow solid. Triturated with Et2O to afford the title compound as a cream solid in 29% yield.

Workup

  1. customThe title compound was prepared
  2. stirringstirring at R.T. for 2 and ½ hours
  3. temperatureIt was cooled in an ice bath
  4. additionbefore adding c
  5. customsolid precipitated out
  6. filtrationFiltered
  7. temperatureheated
  8. temperatureat reflux for 10 minutes
  9. filtrationFiltered hot
  10. customSolvent evaporated
  11. customto afford a pale yellow solid
  12. customTriturated with Et2O

Sources & evidence

ORD record
ord-91a225233d0a441497f926ae59186b9e
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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