Benzyl chloroformate → (2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

HRID 431752

反応式

HRID 431752 の反応式
[OH:1][C@H:2]1[CH2:6][NH:5][C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[OH-].[Na+].[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1.O.C1COCC1>[OH:1][C@H:2]1[CH2:6][N:5]([C:20]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:21])[C@@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1

参加物

6

反応物 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2 回HCID 440014Cis-4-Hydroxy-D-Proline

生成物 1

HCID 688416(2R,4R)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

A suspension of cis4-hydroxy-D-proline (10.0 g) in THF-water (1:1, 100 mL) was added 1N NaOH solution (50 mL) at 5° C. To the mixture was added a solution of benzyloxycarbonyl chloride (12.5 mL) in THF (10 mL) keeping pH to 8.5-10 by the addition of 2N NaOH solution at 5-10° C. After stirring at the same temperature for 1 h, the reaction mixture was washed with EtOAc (50 mL), adjusted to pH 2 by the addition of 4N HCl, and extracted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and evaporated in vacuo to give cis4-hydroxy-N-benzyloxycarbonyl-D-proline (18.74 g).

後処理

  1. washthe reaction mixture was washed with EtOAc (50 mL)
  2. additionadjusted to pH 2 by the addition of 4N HCl
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-051f27377594404abecb19039afecd8c
出典データセット
uspto-grants-2003_12
特許番号
US06660759B1

関連ノート

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