1,1'-Carbonyldiimidazole → HCID 5279008, 화합물

HRID 1157348노트

반응식

HRID 1157348 반응식
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

참가 물질

9

반응물 5

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

생성물 1

HCID 5279008HCID 5279008, 화합물수율 69.4%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 12679Hexamethylphosphoramide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3498e4ae11fa4b08839d261355026f75
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807653B2

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