Hydrochloric Acid → N-Benzoyl-L-proline

HRID 1756040Notes

Reaction equation

HRID 1756040 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>[OH-].[Na+]>[C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 145742L-Proline

Product 1

HCID 6988239N-Benzoyl-L-proline

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a well-stirred solution of L-proline (5.75 g, 0.05 mmole) in 2N NaOH (25 ml), 4N NaOH (12.5 ml) and benzoyl chloride (5.8 ml, 0.05 mole) were added dropwise from different drop funnels, maintaining the temperature near 0°-4° C. The mixture after 15 minutes was acidified with 1N HCl. The resulting oil was extracted with CHCl3, the combined organic extract was dried (MgSO4), and the solvent was removed. Ether was added to the residue and the mixture was allowed to stand overnight at 0° C. The crystals of N-benzoyl-L-proline were separated. Yield 3.42 g (60%), m.p. 152°-154° C., [α]D20 -68.5° (c 0.4; CHCl3); Rf 0.13 (Kiesel-gel, CHCl3 --CH3OH, 9:1). Analysis Calcd. for C12H13NO3 : C, 65.73; H, 5.99; N, 6.39. Found: C, 65.64; H, 6.03; N, 6.54.

Workup

  1. temperaturemaintaining the temperature near 0°-4° C
  2. extractionThe resulting oil was extracted with CHCl3
  3. extractionthe combined organic extract
  4. dry with materialwas dried (MgSO4)
  5. customthe solvent was removed
  6. additionEther was added to the residue
  7. customThe crystals of N-benzoyl-L-proline were separated

Sources & evidence

ORD record
ord-a7265a61893548c7b66523419f58e82a
Source dataset
uspto-grants-1995_08
Patent number
US05439930

Reaction notes

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