HCID 16679760, compound → HCID 16679762, compound

HRID 882316Notes

Reaction equation

HRID 882316 reaction equation
C([NH:4][C@:5]([CH3:15])([C:12]([OH:14])=[O:13])[CH2:6][S:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=O)N>[OH-].[Li+]>[C:8]([S:7][CH2:6][C@@:5]([CH3:15])([C:12]([OH:14])=[O:13])[NH2:4])([CH3:11])([CH3:9])[CH3:10]

Participants

3

Reactant 1

HCID 16679760HCID 16679760, compound

Product 1

HCID 16679762HCID 16679762, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 3939Lithium HydroxideSolvent

Procedure

N-carbamoyl-S-tert-butyl-α-methyl-L-cysteine (82.4 g, 351.4 mmol) was dissolved in a 18% aqueous lithium hydroxide solution (630 g), and the resultant solution was refluxed in nitrogen for 41 hours. After the solution was allowed to cool down to room temperature, the insoluble substance was filtered off, and the filtrate was adjusted to pH 6 by adding conc. hydrochloric acid (180.1 g). After stirring for about 1 hour, the mixture was cooled to 4° C. to 5° C., and further stirred for 1 hour. The produced crystals were filtered off, washed with water, and then dried under reduced pressure to obtain the title compound as a white solid (53.9 g). As a result of HPLC analysis (column: COSMOSIL 5C18-AR (produced by Nacalai Tesque Inc.), mobile phase: potassium dihydrogen phosphate-phosphoric acid solution (pH 2.0)/acetonitrile=90/10, flow rate: 1.0 ml/min, detection wavelength: 210 nm, column temperature: 40° C.), it was confirmed that the solid was the desired compound (yield 85.7%)

Workup

  1. filtrationthe insoluble substance was filtered off
  2. additionby adding conc. hydrochloric acid (180.1 g)
  3. temperaturethe mixture was cooled to 4° C. to 5° C.
  4. stirringfurther stirred for 1 hour
  5. filtrationThe produced crystals were filtered off
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3761ecc8d2a847c8be7ab8670644c8ba
Source dataset
uspto-grants-2015_03
Patent number
US08993800B2

Reaction notes

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