Hydrochloric Acid → L-ornithine mercaptoethansulphonate

HRID 2051524Notes

Reaction equation

HRID 2051524 reaction equation
[SH:1][CH:2]([S:4]([OH:7])(=[O:6])=[O:5])[CH3:3].[NH2:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH2:11][CH2:12][NH2:13].Cl.CO>O>[SH:1][CH:2]([S:4]([OH:7])(=[O:6])=[O:5])[CH3:3].[NH2:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][CH2:11][CH2:12][NH2:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6262L-(-)-OrnithineHCID 14673438Mercaptoethansulphonic acid

Product 1

HCID 86744804L-ornithine mercaptoethansulphonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mercaptoethansulphonic acid coming out from the column, in aqueous solution, under nitrogen stream and at pH=1, is simultaneously added with the stoichiometrical amount of L-ornithine (0.64 g) freed from the hydrochloride through Kastel A 300 resin, in aqueous solution and under nitrogen stream. The addition is carried out at pH values of between 6 and 7. Upon the salification is completed the pH of the solution must be of between 5 and 6. The solution is concentrated to about dryness giving place to a colorless oil which is hot taken with 10 ml of 99% methanol. A conversion to white crystal takes place and the mixture is filtered and dried in oven under vacuum giving 1.117 g; yield 85%; m.p. 187°-192° C.; the pH in 10% aqueous solution is 4.2 and solubility in water is perfect.

Workup

  1. additionThe addition
  2. concentrationThe solution is concentrated to about dryness
  3. customgiving place to a colorless oil which
  4. filtrationthe mixture is filtered
  5. customdried in oven under vacuum
  6. customgiving 1.117 g

Sources & evidence

ORD record
ord-0f5b4c3453db429298d60c09dc6830a9
Source dataset
uspto-grants-1991_05
Patent number
US05019596

Reaction notes

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