Hydrogen Sulfide → Methyl s-phenyl-l-cysteinate

HRID 1248270Notes

Reaction equation

HRID 1248270 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH:4]([N:13]=[N+]=[N-])[CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S>N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:5][S:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:13]

Participants

4

Reactant 2

HCID 402Hydrogen SulfideHCID 13192751Methyl 2-azido-3-(phenylsulfanyl)propanoate

Product 1

HCID 54282006Methyl s-phenyl-l-cysteinateYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

There was led into 6.3 grams (26.6 mmoles) of the 2-azido-3-phenylmercapto-propionic acid methylester produced according to Example 2 in 80 ml of a 50 volume percent aqueous pyridine solution under stirring at 25° C. a weak stream of hydrogen sulfide. After this time the development of gas was ended. The reaction mixture was freed from the pyridine portion on a rotary evaporator under reduced pressure and the aqueous solution remaining behind extracted 3 times, each time with 40 ml of diethyl ether. The combined organic extracts were dried over magnesium sulfate, the ether removed on a rotary evaporator and the residue freed from residual solvent in a high vacuum. Chromatography on a silica gel column with ethyl acetate yielded 5.06 grams (90% of theory) of S-phenyl cysteine methyl ester.

Workup

  1. customproduced
  2. customThe reaction mixture was freed from the pyridine portion on a rotary evaporator under reduced pressure
  3. extractionbehind extracted 3 times
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. customthe ether removed on a rotary evaporator

Sources & evidence

ORD record
ord-d93b55eb646b42858f45d04bdb802743
Source dataset
uspto-grants-1985_06
Patent number
US04523012

Reaction notes

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