Hydrochloric Acid → (2R,2'R)-3,3'-(Hexane-1,6-diyldisulfanediyl)bis(2-aminopropanoic acid)

HRID 1065749Notes

Reaction equation

HRID 1065749 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]OS(C)(=O)=O)(=O)=O.Cl.[NH2:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][SH:21].[OH-:25].[Na+].Cl>O.C(O)C>[CH2:11]([S:21][CH2:20][C@@H:19]([C:22]([OH:23])=[O:25])[NH2:18])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][S:21][CH2:20][C@@H:19]([C:22]([OH:24])=[O:23])[NH2:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 60960Cysteine HydrochlorideHCID 1457351,6-Hexanediol, dimethanesulfonate

Product 1

HCID 53471696(2R,2'R)-3,3'-(Hexane-1,6-diyldisulfanediyl)bis(2-aminopropanoic acid)

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

At 70° C., under nitrogen, a mixture of 137 g of 1,6-hexanediyl dimethanesulfonate and 175.5 g of cysteine-hydrochloride monohydrated in 1.5 l of water containing a little ethanol is agitated. There is then slowly added a solution of 5 N NaOH so that the pH of the reaction mixture is maintained between 8.5 and 9.5. At the end of the reaction the mixture is acidified to pH 5.2 with a solution of HCl. The precipitate is filtered, washed thoroughly with water, then dried and analyzed.

Workup

  1. temperatureis maintained between 8.5 and 9.5
  2. customAt the end of the reaction the mixture
  3. filtrationThe precipitate is filtered
  4. washwashed thoroughly with water
  5. customdried

Sources & evidence

ORD record
ord-6a78a057348846899f816142eb81995d
Source dataset
uspto-grants-1982_05
Patent number
US04331656

Reaction notes

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