Hydrochloric Acid → HCID 12876160, compound

HRID 127293

Reaction equation

HRID 127293 reaction equation
[SH:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][SH:8])=[O:4].[C:14](Cl)(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16].Cl>[OH-].[Na+]>[C:14]([S:8][CH2:7][C@@H:6]([C:9]([OH:11])=[O:10])[NH:5][C:3](=[O:4])[C:2]([S:1][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:12])(=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 62493Pivaloyl chlorideHCID 656604Bucillamine

Product 1

HCID 12876160HCID 12876160, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

N-(2-Mercapto-2-methylpropanoyl)-L-cysteine (11.2 g, 0.05 mol) is dissolved in N sodium hydroxide (50 ml) and pivaloyl chloride (17.0 g, 0.13 mol) and aqueous N sodium hydroxide (150 ml) are added dropwise at 0° C. with stirring under a nitrogen atmosphere. After the addition, the mixture is stirred for 1 hour at room temperature and acidified with 6 N hydrochloric acid. The produced oil is extracted with ethyl acetate and the organic layer is washed with water, dried and concentrated to dryness under reduced pressure to yield 3.2 g (16.4%) of S-pivaloyl-N-(S-pivaloyl-2-mercapto-2-methylpropanoyl)-L-cysteine.

Workup

  1. additionare added dropwise at 0° C.
  2. additionAfter the addition
  3. stirringthe mixture is stirred for 1 hour at room temperature
  4. extractionThe produced oil is extracted with ethyl acetate
  5. washthe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7c4dd1599f7b4ac3a70bf509b882be75
Source dataset
uspto-grants-1981_03
Patent number
US04255446

Linked notes

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