1,1'-Carbonyldiimidazole → HCID 5279008、化合物

HRID 1157348ノート

反応式

HRID 1157348 の反応式
C([NH+](CC)CC)C.[N:8]([C@@H:11]1[C@@H:15]([CH2:16][P:17]([OH:20])(=[O:19])[OH:18])[O:14][C@@H:13]([N:21]2[CH:29]=[C:27]([CH3:28])[C:25](=[O:26])[NH:24][C:22]2=[O:23])[CH2:12]1)=[N+:9]=[N-:10].C(N1C=CN=C1)(N1C=CN=C1)=O.C([NH+](CCCC)CCCC)CCC.[O-:55][P:56]([NH:59][P:60]([O-])([O-:62])=[O:61])(=[O:58])[O-:57]>CN(P(N(C)C)(N(C)C)=O)C.O.CO>[CH3:28][C:27]1[C:25](=[O:26])[NH:24][C:22](=[O:23])[N:21]([C@@H:13]2[O:14][C@H:15]([CH2:16][P:17]([O:18][P:60]([OH:62])([NH:59][P:56]([OH:58])([OH:57])=[O:55])=[O:61])([OH:20])=[O:19])[C@@H:11]([N:8]=[N+:9]=[N-:10])[CH2:12]2)[CH:29]=1

参加物

9

反応物 5

HCID 682631,1'-CarbonyldiimidazoleHCID 4725903'-Azido-3',5'-dideoxythymidine-5'-phosphonic acidHCID 1385867TriethylammoniumHCID 3724478TributylammoniumHCID 23278979Imidodiphosphate

生成物 1

HCID 5279008HCID 5279008、化合物収率 69.4%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 12679Hexamethylphosphoramide溶媒2 回

実験手順

The triethylammonium salt of compound 53 (50.0 mg, 0.09 mmol) was dissolved in HMPA (2 mL) and 1,1′-carbonyldiimidazole (106 mg, 0.66 mmol) was added at room temperature and stirred for 2 h. Methanol (35 μL) was added and stirring was continued for 45 min. The tri-n-butylammonium salt of imidodiphosphate (427 mg, 0.46 mmol) dissolved in HMPA (2 mL) was added with syringe to the solution of activated AZT monophosphate, and the combined solution was stirred at room temperature for 4 h. The reaction mixture was cooled in ice-bath and water (5 mL) was added. Purification by HPLC gave 30.6 mg of the titled compound 57.

後処理

  1. stirringstirring
  2. waitwas continued for 45 min
  3. stirringthe combined solution was stirred at room temperature for 4 h
  4. temperatureThe reaction mixture was cooled in ice-bath
  5. customPurification by HPLC

出典と根拠

ORDレコード
ord-3498e4ae11fa4b08839d261355026f75
出典データセット
uspto-grants-2010_10
特許番号
US07807653B2

反応ノート

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