Acetyl chloride → 3-Acetyl-3'-azido-5'-O-(3-chlorobenzoyl)-3'-deoxythymidine

HRID 973795노트

반응식

HRID 973795 반응식
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][O:10][C:11](=[O:19])[C:12]2[CH:17]=C[C:15](Cl)=[CH:14][CH:13]=2)[O:7][C@@H:6]([N:20]2[CH:28]=[C:26]([CH3:27])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[CH2:5]1)=[N+:2]=[N-:3].[C:29](Cl)(=[O:31])[CH3:30].[CH:33]([Cl:36])(Cl)Cl.CO>C1C=CC=CC=1.[Ag]C#N>[C:29]([N:23]1[C:24](=[O:25])[C:26]([CH3:27])=[CH:28][N:20]([C@@H:6]2[O:7][C@H:8]([CH2:9][O:10][C:11](=[O:19])[C:12]3[CH:13]=[CH:14][CH:15]=[C:33]([Cl:36])[CH:17]=3)[C@@H:4]([N:1]=[N+:2]=[N-:3])[CH2:5]2)[C:21]1=[O:22])(=[O:31])[CH3:30]

참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 186478033'-azido-5'-O-(4-chlorobenzoyl)-3'-deoxythymidineHCID 21584188Chloroform methanol

생성물 1

HCID 186477993-Acetyl-3'-azido-5'-O-(3-chlorobenzoyl)-3'-deoxythymidine수율 64%

시약·촉매·용매 2

HCID 178509332CID 101611454촉매HCID 241Benzene용매

실험 절차

To a mixture of 3'-azido-5'-O-(4-chlorobenzoyl)-3'-deoxythymidine (0.3 g, 0.74 mMol) and silver cyanide (0.4 g, 3.0 mMol) in 20 mL of benzene, excess acetyl chloride (2.6 g, 33 mMol) was added in several portions. The mixture was stirred at room temperature until the starting material disappeared (4 hours) as established by TLC CHCl3 /MeOH 20:1 (v/v). The reaction was filtered and the filtrate evaporated under reduced pressure to dryness. The resulting oily residue was chromatographed on silica gel eluted with chloroform/hexane 1:1 (v/v) followed by chloroform to give 0.21 g (64%) of the desired product as an oil.

후처리

  1. additionwas added in several portions
  2. custom(4 hours)
  3. filtrationThe reaction was filtered
  4. customthe filtrate evaporated under reduced pressure to dryness
  5. customThe resulting oily residue was chromatographed on silica gel
  6. washeluted with chloroform/hexane 1:1 (v/v)

출처 및 근거

ORD 기록
ord-bec77de7f2084b37aec0e6dc988af035
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05064946

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