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

HRID 1756040ノート

反応式

HRID 1756040 の反応式
[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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 145742L-Proline

生成物 1

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

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a7265a61893548c7b66523419f58e82a
出典データセット
uspto-grants-1995_08
特許番号
US05439930

反応ノート

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