Hydrochloric Acid → (2S)-1-benzoylpyrrolidine-2-carboxylic acid

HRID 1756040노트

반응식

HRID 1756040 반응식
[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

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 145742L-Proline

생성물 1

HCID 6988239(2S)-1-benzoylpyrrolidine-2-carboxylic acid

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a7265a61893548c7b66523419f58e82a
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05439930

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