HCID 121714, compound → L-cysteinesulfinic acid

HRID 342166Notes

Reaction equation

HRID 342166 reaction equation
C(S[S:8]([CH2:11][CH:12]([NH2:16])[C:13]([OH:15])=[O:14])(=[O:10])=[O:9])C(N)C(O)=O>C(O)=O>[CH2:11]([S:8]([OH:10])=[O:9])[C@H:12]([NH2:16])[C:13]([OH:15])=[O:14]

Participants

3

Reactant 1

HCID 121714HCID 121714, compound

Product 1

HCID 1549098L-cysteinesulfinic acidYield 113.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

This cystine disulfoxide (13.6 g, 0.05 mols) was dissolved in 250 ml of formic acid. The solution was passed through 150 ml of a Diaion SK1B column, and washed with 300 ml of water. A solution of 11.4 g of sodium hydroxide in 200 ml of water was passed through this resin column, and then washed with 150 ml of water. Subsequently, a solution of 17.5 g of a 25% aqueous ammonia in 200 ml of water was passed through the resin column, and then washed with water. This eluate was passed through 150 ml of a Diaion WK-10 column. The resulting eluate was concentrated, crystallized, filtered and dried to obtain 8.7 g of cysteinesulfinic acid (yield: 85%).

Workup

  1. washwashed with 300 ml of water
  2. washwashed with 150 ml of water
  3. washwashed with water
  4. concentrationThe resulting eluate was concentrated
  5. customcrystallized
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-f72852b33c684024acef40b5afbfcfda
Source dataset
uspto-grants-1999_01
Patent number
US05856563

Reaction notes

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