Hydrochloric Acid → HCID 71184004, compound

HRID 2371009Notes

Reaction equation

HRID 2371009 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CO>[CH2:18]([NH:2][C@@H:3]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:4]([OH:6])=[O:5])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 10340Sodium CarbonateHCID 12832742L-Aspartic acid, 4-methyl ester, hydrochloride (1:1)

Product 1

HCID 71184004HCID 71184004, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 10 g (S)-2-amino-4-methoxy-4-oxobutanoic acid hydrochloride in 400 ml methanol was added 15 g sodium carbonate, and the mixture was stirred at 25° C. Twenty (20) g benzyl chloride was then added dropwise at this temperature. After completion of the reaction, the mixture was maintained at this temperature for 12 h. The reaction solution was neutralized with a diluted aqueous hydrochloride acid solution to produce a neutralized solution. Methanol was evaporated, and the residue was partitioned and extracted with ethyl acetate. The organic layer was concentrated and then washed with water 2˜3 times to afford 16 g crude (S)-2-(benzylamino)-4-methoxy-4-oxobutanoic acid, with a yield of 91.3%.

Workup

  1. additionwas then added dropwise at this temperature
  2. customAfter completion of the reaction
  3. temperaturethe mixture was maintained at this temperature for 12 h
  4. customto produce a neutralized solution
  5. customMethanol was evaporated
  6. customthe residue was partitioned
  7. extractionextracted with ethyl acetate
  8. concentrationThe organic layer was concentrated
  9. washwashed with water 2˜3 times

Sources & evidence

ORD record
ord-9ebefeb6d0af41f6acb197780d7653a7
Source dataset
uspto-grants-2014_04
Patent number
US08710255B2

Reaction notes

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