Hydrochloric Acid → N-benzoyl-L-alanine

HRID 1659357Notes

Reaction equation

HRID 1659357 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>[OH-].[Na+]>[C:7]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 7412Benzoyl chloride

Product 1

HCID 709778N-benzoyl-L-alanine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

L-alanine (17.8 g., 0.2 mole) was dissolved in 2N-sodium hydroxide solution (120 ml.) with cooling to 0°-5° C. Benzoyl chloride (30.0 g., 0.22 mole), followed by 2N-sodium hydroxide (120 ml.), were then added to the solution in ten equal and alternate portions with vigorous intermittent shaking and ice cooling. The mixture was continually maintained at an alkaline pH. After completion of the addition, the mixture was shaken for 15 minutes at room-temperature. The clear solution obtained was acidified with concentrated hydrochloric acid to pH2 whilst ice cooling to give N-benzoyl L-alanine as a solid (27.8 g.), m.p. 137°-139° C.

Workup

  1. temperaturewith cooling to 0°-5° C
  2. additionwere then added to the solution in ten equal
  3. temperatureThe mixture was continually maintained at an alkaline pH
  4. additionAfter completion of the addition
  5. stirringthe mixture was shaken for 15 minutes at room-temperature
  6. customThe clear solution obtained

Sources & evidence

ORD record
ord-6b55e5cc5b1b4f4db225d3dec22b3c21
Source dataset
uspto-grants-1981_12
Patent number
US04303649

Reaction notes

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