Dichloromethane → 2',3'-Bis-o-(tert-butyldimethylsilyl)-5'-deoxy-5-iodo-n4-(n-pentyloxycarbonyl)cytidine

HRID 321932노트

반응식

HRID 321932 반응식
[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@@H:12]([CH3:22])[O:11][C@H:10]1[N:23]1[CH:30]=[C:29]([I:31])[C:27]([NH2:28])=[N:26][C:24]1=[O:25])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)Cl.Cl[C:36]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:37]>>[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:20])([CH3:21])[CH3:19])([CH3:17])[CH3:16])[C@@H:12]([CH3:22])[O:11][C@H:10]1[N:23]1[CH:30]=[C:29]([I:31])[C:27]([NH:28][C:36]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:37])=[N:26][C:24]1=[O:25])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

참가 물질

4

반응물 3

HCID 6344DichloromethaneHCID 69489Pentyl chloroformateHCID 153827345'-Deoxy-2',3'-bis-o-(tert-butyldimethylsilyl)-5-iodocytidine

생성물 1

HCID 539224752',3'-Bis-o-(tert-butyldimethylsilyl)-5'-deoxy-5-iodo-n4-(n-pentyloxycarbonyl)cytidine수율 91%

실험 절차

To a stirred solution of 5′-deoxy-2′,3′-bis-O-(tert-butyldimethylsilyl)-5-iodocytidine (116 mg, 0.200 mmol) in CH2Cl2 (2 ml) pyridine (84 μl, 1.00 mmol), N,N-dimethylamino-pyridine (6 mg, 0.05 mmol), and n-pentyl chloroformate (95 μl, 0.600 mmol) was added at room temperature under Ar. After stirring for 30 minutes, the reaction mixture was partitioned with dichloromethane and water and the organic phase was separated and the water phase was extracted with CH2Cl2 (15 ml×4). The combined organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was evaporated under reduced pressure. The crude product was purified by flash chromatography on SiO2 (eluent: 20% EtOAc/n-hexane) to give 2′,3′-bis-O-(tert-butyldimethylsilyl)-5′-deoxy-5-iodo-N4-(n-pentyloxycarbonyl)cytidine as a colorless amorphous solid. (132.4 mg, 91% yield).

후처리

  1. customthe reaction mixture was partitioned with dichloromethane and water
  2. customthe organic phase was separated
  3. extractionthe water phase was extracted with CH2Cl2 (15 ml×4)
  4. washThe combined organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated under reduced pressure
  8. customThe crude product was purified by flash chromatography on SiO2 (eluent: 20% EtOAc/n-hexane)

출처 및 근거

ORD 기록
ord-9924fd1c10db4cccb11c551d92340aed
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211166B1

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