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Sodium Azide → N2 (benzyloxycarbonyl)-4(R)-azido-N1-tert.butyl-L-prolinamide

HRID 742897
ノート
印刷プレビュー

反応式

HRID 742897 の反応式
N#N.[CH2:3]([O:10][C:11]([C@@:13]1([C:27]([NH2:29])=[O:28])[CH2:17][C@H:16](OS(C)(=O)=O)[CH2:15][N:14]1[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N-:30]=[N+:31]=[N-:32].[Na+]>CN(C)C=O>[N:30]#[N:31].[CH2:3]([O:10][C:11]([C@@:13]1([C:27]([NH2:29])=[O:28])[CH2:17][C@@H:16]([N:30]=[N+:31]=[N-:32])[CH2:15][N:14]1[C:23]([CH3:24])([CH3:26])[CH3:25])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 33557Sodium AzideHCID 86746278N2 (benzyloxycarbonyl)-N1-tert.butyl-4(S)-(methanesulphonyloxy)-L-prolinamide

生成物 1

HCID 86746282N2 (benzyloxycarbonyl)-4(R)-azido-N1-tert.butyl-L-prolinamide収率 78.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

0.5 g Of N2 -(benzyloxycarbonyl)-N1 -tert.butyl-4(S)-(methanesulphonyloxy)-L-prolinamide was dissolved in 10 ml of dry dimethylformamide and treated with 0.330 g of sodium azide. The heterogeneous mixture was stirred and heated at 75° C. for 18 hours. The mixture was evaporated under an oil pump vacuum to give a solid which was partitioned between ethyl acetate and water. The ethyl acetate phase was washed with saturated sodium chloride solution and dried over anhydrous sodium sulphate. The solvent was removed by evaporation to give 0.345 g of N2 -(benzyloxycarbonyl)-4(R)-azido-N1 -tert.butyl-L-prolinamide in the form of a gum.

後処理

  1. customThe mixture was evaporated under an oil pump vacuum
  2. customto give a solid which
  3. customwas partitioned between ethyl acetate and water
  4. washThe ethyl acetate phase was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe solvent was removed by evaporation

出典と根拠

ORDレコード
ord-8f21c632608b4d80ab7cf5af1eaa4658
出典データセット
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05554756

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート