Chromic Acid → N-Carbobenzyloxy-4-keto-L-proline

HRID 848446

反応式

HRID 848446 の反応式
[C:1]([N:11]1[CH2:18][CH:17]([OH:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[Cr](O)(O)(=O)=O>CC(C)=O.S(=O)(=O)(O)O>[C:1]([N:11]1[CH2:18][C:17](=[O:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

参加物

5

反応物 2

HCID 24425Chromic AcidHCID 12731799(2S)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

生成物 1

HCID 11076282N-Carbobenzyloxy-4-keto-L-proline収率 10.7%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 1118Sulfuric Acid溶媒

実験手順

21.5 g. (0.81 mole) of N-carbobenzyloxy-4-hydroxy-L-proline is oxidized in 1.2 liters of acetone with 83 ml. of 8 N chromic acid in sulfuric acid as described in J.A.C.S.79, 189 (l957). In order to facilitate the subsequent filtration of chromium salts, 30 g. of Celite (diatomaceous earth) is added to the acetone solution before introduction of the oxidizing agent. An air stirrer is employed. The reaction mixture is filtered and the acetone filtrate is concentrated to approximately 300 ml. before diluting with 1 liter of chloroform. The solution is washed with 300 ml. of saturated sodium chloride (four times), dried (MgSO4), filtered and the solvent evaporated to give N-carbobenzyloxy-4-keto-L-proline (22.8 g.) which is crystallized from ether (50 ml.)-hexane (150 ml.) to obtain 17.2 g. (81%) of product, m.p. 99°-101°, [α]D26 +17° (c, 1% in chloroform).

後処理

  1. filtrationthe subsequent filtration of chromium salts, 30 g
  2. additionof Celite (diatomaceous earth) is added to the acetone solution before introduction of the oxidizing agent
  3. customAn air stirrer is employed
  4. filtrationThe reaction mixture is filtered
  5. concentrationthe acetone filtrate is concentrated to approximately 300 ml
  6. additionbefore diluting with 1 liter of chloroform
  7. washThe solution is washed with 300 ml
  8. dry with materialof saturated sodium chloride (four times), dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent evaporated

出典と根拠

ORDレコード
ord-b4461bb6bb16476f91ec5180928dc8ec
出典データセット
uspto-grants-1981_10
特許番号
US04296113

関連ノート

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