Potassium Carbonate → N-(Morpholinocarbonyl)-L-phenylalanine S-methyl-L-cysteine

HRID 1087314Notes

Reaction equation

HRID 1087314 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:8])[CH2:3][CH2:2]1.C[O:22][C:23](=[O:29])[C@H:24]([CH2:26][S:27][CH3:28])[NH2:25].C(=O)([O-])[O-].[K+].[K+]>O.CO>[O:1]1[CH2:6][CH2:5][N:4]([C:7]([NH:9][C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])[CH2:3][CH2:2]1.[CH3:28][S:27][CH2:26][C@@H:24]([C:23]([OH:29])=[O:22])[NH2:25]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67865905N-(Morpholinocarbonyl)-L-phenylalanine S-methyl-L-cysteine methyl ester

Product 1

HCID 67865833N-(Morpholinocarbonyl)-L-phenylalanine S-methyl-L-cysteineYield 89.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To an ice-cooled solution of 1.15 g N-(morpholinocarbonyl)-L-phenylalanine-S-methyl-L-cysteine methyl ester in 30 mL water and 60 mL methanol was added 3.5 g potassium carbonate. The resulting mixture was stirred at 0° for 15 min. and at ambient temperature for 4 h. The solution was concentrated in vacuo to an aqueous solution, which was acidified with conc. hydrochloric acid and extracted 3×50 mL methylene chloride. The combined extracts were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 1.0 g (89%) of the crude acid.

Workup

  1. concentrationThe solution was concentrated in vacuo to an aqueous solution, which
  2. extractionextracted 3×50 mL methylene chloride
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-021a9cae8b804880bd3477362a515fb7
Source dataset
uspto-grants-1991_07
Patent number
US05034376

Reaction notes

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