Acetic Anhydride → O-Acetyldeoxyacyclovir

HRID 64627노트

반응식

HRID 64627 반응식
[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.[C:16](OC(=O)C)(=[O:18])[CH3:17]>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:16]([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])[CH3:17]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 55256Desciclovir

생성물 1

HCID 10422259O-Acetyldeoxyacyclovir

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

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 anhydride 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.

후처리

  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

출처 및 근거

ORD 기록
ord-36d240ac62694166b65b0e5066e56183
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609662

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