Triethylamine → Benzyl 3-(alpha-azidoacetoxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 1164337ノート

反応式

HRID 1164337 の反応式
[N:1]([CH2:4][C:5](Cl)=[O:6])=[N+:2]=[N-:3].C(N(CC)CC)C.[N:15]12[C:21](=[O:22])[CH2:20][CH:19]1[CH2:18][C:17](=[O:23])[CH:16]2[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C(Cl)Cl>[N:1]([CH2:4][C:5]([O:23][C:17]1[CH2:18][CH:19]2[N:15]([C:21](=[O:22])[CH2:20]2)[C:16]=1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:6])=[N+:2]=[N-:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 109095582-azidoacetyl ChlorideHCID 12804725Benzyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

生成物 1

HCID 15136298Benzyl 3-(alpha-azidoacetoxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Azidoacetyl chloride (21 μl) is added by syringe in an ice-cold, stirring solution of triethylamine (42 μl) and benzyl 1-azabicyclo[3.2.0]heptane-3,7-dione-2-carboxylate (52 mg) in anhydrous methylene chloride (2 ml). After stirring 30 mins in the cold, the reaction mixture is diluted with methylene chloride (5 ml), washed with H2O (2 ml), pH 3 phosphate buffer (2 ml), and 5% NaHCO3 (2 ml), dried with MgSO4, filtered, and evaporated in vacuo. Chromatography of the residue on a silica gel GF plate gives benzyl 3-(α-azidoacetoxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

後処理

  1. washwashed with H2O (2 ml), pH 3 phosphate buffer (2 ml), and 5% NaHCO3 (2 ml)
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

出典と根拠

ORDレコード
ord-a5f67516a9ca4799a8b53c26502b988c
出典データセット
uspto-grants-1983_01
特許番号
US04369187

反応ノート

読み込み中…