Sodium Hydroxide → HCID 15058527, compound

HRID 1088617Notes

Reaction equation

HRID 1088617 reaction equation
C([O:8][C:9](=[O:27])[C@H:10]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:11][C:12]([N:14]1[CH2:19][CH2:18][S:17][CH2:16][CH2:15]1)=[O:13])C1C=CC=CC=1.[OH-].[Na+]>CO.O>[S:17]1[CH2:18][CH2:19][N:14]([C:12]([NH:11][C@H:10]([C:9]([OH:27])=[O:8])[CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:13])[CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15058528HCID 15058528, compound

Product 1

HCID 15058527HCID 15058527, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-thiomorpholinocarbonyl-L-phenylalanine benzyl ester (526 mg) in a mixture of methanol (10 ml) and water (10 ml) which was cooled to 0° C., was added lN sodium hydroxide solution (4 ml). The mixture was stirred at the same temperature for 1 hour. After evaporation of methanol, remaining aqueous solution was washed with diethyl ether, acidified to pH 2.5 with 3N hydrochloric acid and extracted with ethyl acetate (30 ml×3). The extract was washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure to give N-thiomorpholinocarbonyl-L-phenylalanine (382 mg) as an oil.

Workup

  1. customAfter evaporation of methanol
  2. washwas washed with diethyl ether
  3. extractionextracted with ethyl acetate (30 ml×3)
  4. washThe extract was washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-60a1556a2e954de39a4a037ff4ab9214
Source dataset
uspto-grants-1990_10
Patent number
US04963530

Reaction notes

Loading…