Chloroacetyl chloride → (3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid

HRID 1366556Notes

Reaction equation

HRID 1366556 reaction equation
[CH2:1]([NH:8][C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:16][C:17](Cl)=[O:18]>[OH-].[Na+]>[O:18]=[C:17]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][O:11][CH2:16]1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 853606(2S)-2-(benzylamino)-3-hydroxypropanoic acid

Product 1

HCID 13543372(3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acidYield 19%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a 0° C. solution of N-benzylserine (19.15 g, 105.7 mmol) in 2 N aq. NaOH (100 mL) was added chloroacetyl chloride (10.2 mL, 126.4 mmol) dropwise, and the solution was stirred for 45 min. To the solution was added 30% aq. NaOH (40 mL) dropwise, and the reaction was stirred for 1 h, and then stirred and warmed to room temperature for 72 h. The reaction was adjusted to pH 1 and extracted with three portions of EtOAc. The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was washed with EtOAc/hexane to give (3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (4.61 g, 19% yield).

Workup

  1. stirringthe reaction was stirred for 1 h
  2. stirringstirred
  3. extractionextracted with three portions of EtOAc
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with EtOAc/hexane

Sources & evidence

ORD record
ord-d9d6e383901144a08093e3fc7bb75400
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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