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

HRID 45586Notes

Reaction equation

HRID 45586 reaction equation
[CH2:1]([NH:8][C@@H:9]([CH2:13][OH:14])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][C:23](Cl)=[O:24].[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH2:1]([N:8]1[C:23](=[O:24])[CH2:22][O:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 853606(2S)-2-(benzylamino)-3-hydroxypropanoic acid

Product 1

HCID 13543372(3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acidYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(benzylamino)-3-hydroxypropanoic acid (40.0 g, 205 mmol) in tetrahydrofuran (600 mL) was added aqueous potassium carbonate solution (85.0 g, 600 mL) at 0° C. under nitrogen atmosphere, and additionally, chloroacetylchloride (29.0 mL, 369 mmol) was added. After stirring for 2 hours at room temperature, to the mixture was added 30% aqueous sodium hydroxide solution to adjust to pH 13. To the mixture was added diethyl ether, and the organic layer was separated, and then concentrated hydrochloric acid was added to adjust to pH 1, and cooled to 0° C. The precipitated crystal was collected by filtration to give the title compound (29.0 g, 123 mmol, 60%).

Workup

  1. customthe organic layer was separated
  2. additionconcentrated hydrochloric acid was added
  3. temperaturecooled to 0° C
  4. filtrationThe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-07d8faf7d6a948c1a8421e53d31523de
Source dataset
uspto-grants-2013_09
Patent number
US08541585B2

Reaction notes

Loading…