Desciclovir → O-Acetyldeoxyacyclovir

HRID 1252682ノート

反応式

HRID 1252682 の反応式
[OH:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][C:9]([NH2:15])=[N:10][CH:11]=2.[CH3:16][C:17](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:18]>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:17]([O:1][CH2:2][CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:7]1=[N:8][C:9]([NH2:15])=[N:10][CH:11]=2)(=[O:18])[CH3:16]

参加物

5

反応物 2

HCID 55256DesciclovirHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

生成物 1

HCID 10422259O-Acetyldeoxyacyclovir

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 0.82 g (3.92 mM) of 9-(2-hydroxyethoxymethyl)-2-amino-9H-purine, 48 mg (0.392 mM) of a 4-dimethylaminopyridine and 0.75 ml (7.84 mM) of acetic anhyride in 18 ml of dry dimethylformamide was stirred at room temperature for two days. The reaction mixture was evaporated in vacuo and the residue dissolved in ethyl acetate and absorbed on silica gel. The solvent was removed by flash evaporation and the residual powder added to a column prepared for flash chromatography. Elution with 5% methanol in dichloromethane gave 1.0 g of a semicrystalline oil which on recrystallization from benzene-hexane gave analytically pure 9-(2-acetoxyethoxymethyl)-2-amino-9H-purine, mpt. 115°-118° C. An additional crop was obtained from the mother liquor.

後処理

  1. customThe reaction mixture was evaporated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. customabsorbed on silica gel
  4. customThe solvent was removed by flash evaporation
  5. additionthe residual powder added to a column
  6. customprepared for flash chromatography
  7. washElution with 5% methanol in dichloromethane
  8. customgave 1.0 g of a semicrystalline oil which
  9. customon recrystallization from benzene-hexane

出典と根拠

ORDレコード
ord-e230f6b81633455cb4f47dbfbdc7db06
出典データセット
uspto-grants-1988_05
特許番号
US04745119

反応ノート

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