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

HRID 973795ノート

反応式

HRID 973795 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178509332CID 101611454触媒HCID 241Benzene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bec77de7f2084b37aec0e6dc988af035
出典データセット
uspto-grants-1991_11
特許番号
US05064946

反応ノート

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