(+-)-Methionine → HCID 178515872, compound

HRID 2120273

Reaction equation

HRID 2120273 reaction equation
NC(C(O)=O)CCSC.C[O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:22]=[CH:21][NH:20][N:19]=2)=[CH:14][CH:13]=1.CS(O)(=O)=O.[OH-].[Na+]>O>[NH:20]1[CH:21]=[CH:22][C:18]([C:15]2[CH:16]=[CH:17][C:12]([OH:11])=[CH:13][CH:14]=2)=[N:19]1

Participants

6

Reactant 4

HCID 876(+-)-MethionineHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 178488674HCID 178488674, compound

Product 1

HCID 178515872HCID 178515872, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a round-bottomed flask was added D,L-methionine (1.19 g, 7.96 mmol), 3-(4-methoxyphenyl)-pyrazole (990 mg, 5.68 mmol), and methanesulfonic acid (23 ml). The resulting solution was heated to about 50° C. for about forty-eight hours, and was then allowed to cool to room temperature and poured into water. The pH of the solution was adjusted to about 7 with 5 N sodium hydroxide, and was then extracted with ethyl acetate. The organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 950 mg of a white solid which was determined to be about 95% pure by NMR. This material was subsequently employed directly without further purification.

Workup

  1. temperatureto cool to room temperature
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c350c59d444f40a9ae5cfd31ef20114d
Source dataset
uspto-grants-2004_02
Patent number
US06689888B2

Linked notes

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