Hydrochloric Acid → 5-oxothiomorpholine-3-carboxylic Acid

HRID 1085624Notes

Reaction equation

HRID 1085624 reaction equation
O.Cl.[NH2:3][C@H:4]([C:7]([OH:9])=[O:8])[CH2:5][SH:6].C(=O)([O-])[O-].[Na+].[Na+].I[CH2:17][C:18](N)=[O:19].Cl>O>[O:19]=[C:18]1[NH:3][CH:4]([C:7]([OH:9])=[O:8])[CH2:5][S:6][CH2:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3727IodoacetamideHCID 10340Sodium Carbonate2×HCID 23462L-Cysteine hydrochloride monohydrate

Product 1

HCID 35566975-oxothiomorpholine-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.75 g (10 mmole) of L-cysteine hydrochloride monohydrate dissolved in 50 ml of water was adjusted to pH 8.0 with 1M sodium carbonate. Under nitrogen gas stream, 1.85 g (10 mmole) of monoiodoacetamide and 1M sodium carbonate were added alternately while maintaining pH at 8.0. After the reaction was carried out at room temperature for 1 hour, further the reaction was carried out in a sealed tube at 100° C. for 2 hours. To the reaction mixture was added 4N HCl to adjust the pH to 3.25, followed by concentration to dryness. The residue was extracted with hot ethanol, and after cooling, the crystals were collected by filtration and recrystallized from hot ethanol. Yield: 560 mg (34.8%), melting point: 182° to 184° C., Fab mass analysis [M+H]+= 162.

Workup

  1. temperaturewhile maintaining pH at 8.0
  2. waitfurther the reaction was carried out in a sealed tube at 100° C. for 2 hours
  3. concentrationfollowed by concentration to dryness
  4. extractionThe residue was extracted with hot ethanol
  5. temperatureafter cooling
  6. filtrationthe crystals were collected by filtration
  7. customrecrystallized from hot ethanol

Sources & evidence

ORD record
ord-5f73d798f8ad4b57a89f9a7d3d9c9788
Source dataset
uspto-grants-1991_04
Patent number
US05010174

Reaction notes

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