Hydrochloric Acid → HCID 11346957, compound

HRID 1609772Notes

Reaction equation

HRID 1609772 reaction equation
C[O:2][C:3](=[O:22])[C@H:4]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:5][C:6](=[O:14])[C@@H:7]([C:9]([CH2:12][OH:13])([CH3:11])[CH3:10])[OH:8].Cl>CO.[OH-].[Na+]>[C:6]([NH:5][C@H:4]([C:3]([OH:22])=[O:2])[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:14])[C@@H:7]([C:9]([CH2:12][OH:13])([CH3:10])[CH3:11])[OH:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15280426HCID 15280426, compound

Product 1

HCID 11346957HCID 11346957, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of pantoylphenylalanine methyl ester (0.85 g, 2.7 mmol) in methanol, 3.85 ml of 1.00M sodium hydroxide was added very slowly, with stirring. The progress of the hydrolysis was monitored by TLC. After 18 h, the reaction mixture was acidified by the addition of 3.9 ml of 1.00M hydrochloric acid to pH 3.2, concentrated on a rotary evaporator, and diluted with ethyl acetate. The phases were separated, and the aqueous solution was extracted with additional ethyl acetate. The combined organic extracts were dried voer anhydrous sodium sulfate, gravity filtered, the solvent removed on a rotary evaporator. The resulting white solid was dried in a vacuum oven (65° C., 0.2 mm Hg, 24 h), to yield pantoylphenylalanine (0.78 g).

Workup

  1. concentrationconcentrated on a rotary evaporator
  2. additiondiluted with ethyl acetate
  3. customThe phases were separated
  4. extractionthe aqueous solution was extracted with additional ethyl acetate
  5. dry with materialThe combined organic extracts were dried voer anhydrous sodium sulfate, gravity
  6. filtrationfiltered
  7. customthe solvent removed on a rotary evaporator
  8. customThe resulting white solid was dried in a vacuum oven (65° C., 0.2 mm Hg, 24 h)

Sources & evidence

ORD record
ord-919f400e657d4b0c8feae4828fdcc076
Source dataset
uspto-grants-1995_03
Patent number
US05401880

Reaction notes

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