Sodium Hydroxide → 5-oxothiomorpholine-3-carboxylic Acid

HRID 866530Notes

Reaction equation

HRID 866530 reaction equation
[C:1]([CH2:4][S:5][CH2:6][C@@H:7]([C:9]([OH:11])=[O:10])[NH2:8])(O)=[O:2].[OH-].[Na+]>O>[O:2]=[C:1]1[NH:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6][S:5][CH2:4]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 193653S-(Carboxymethyl)-L-cysteine

Product 1

HCID 35566975-oxothiomorpholine-3-carboxylic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 40 ml. of water is suspended 3.6 g (0.02 M) of S-carboxymethyl-L-cysteine, followed by addition of 20 ml. of 1N-NaOH. The reaction is conducted in a sealed tubular reactor at 110° C for 48 hours. The reaction mixture is passed through a column (4.5 × 12.0 cm) of Amberlite IR-120 B (H+ -form), whereby it is desalted. The effluent is concentrated to dryness and the residue is dissolved in glacial acetic acid. Following addition of ether, the resultant crystals are recovered by filtration. Yield 1.55 g. (48.1%); melting point: 152.0°-153.0° C; optical rotation [α]D25 + 1.1° (c=0.64, in water).

Workup

  1. additionfollowed by addition of 20 ml
  2. concentrationThe effluent is concentrated to dryness
  3. dissolutionthe residue is dissolved in glacial acetic acid
  4. additionaddition of ether
  5. filtrationthe resultant crystals are recovered by filtration
  6. customoptical rotation [α]D25 + 1.1° (c=0.64, in water)

Sources & evidence

ORD record
ord-8c1dd6754a484b708e59fbd6d789d3f5
Source dataset
uspto-grants-1978_07
Patent number
US04100152

Reaction notes

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