Hydrochloric Acid → Uridine, 3'-azido-5-chloro-2',3'-dideoxy-

HRID 973791

반응식

HRID 973791 반응식
[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:18]=[CH:17][C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3].Cl.[Cl:20]C1C=CC=C(C(OO)=O)C=1.O>CC(N(C)C)=O>[N:1]([C@@H:4]1[C@@H:8]([CH2:9][OH:10])[O:7][C@@H:6]([N:11]2[CH:18]=[C:17]([Cl:20])[C:15](=[O:16])[NH:14][C:12]2=[O:13])[CH2:5]1)=[N+:2]=[N-:3]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 55262NavuridineHCID 70297m-Chloroperbenzoic acid

생성물 1

HCID 451479Uridine, 3'-azido-5-chloro-2',3'-dideoxy-

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

반응 조건

온도
0 °C

실험 절차

3'-Azido-2',3'-dideoxyuridine (0.25 g; 1 mMol) was dissolved in 2 mL dry dimethylacetamide (DMAC), cooled to 0° C. and 2 mL of 0.5M HCl in DMAC was added. m-Chloroperbenzoic acid (0.277 g; 1.6 mMol) was added in two portions over ten minutes and the mixture was allowed to come to ambient temperature. After two hours, 4 mL H2O was added and the solution filtered. The aqueous DMAC solution was extracted with Et2O (3×3 mL) and the Et2O was evaporated in vacuo to an oil which was applied to a silica gel column. Elution with CHCl3MeOH (15:1 v/v), combination of the appropriate fractions and evaporation in vacuo yielded an oil which was crystallized from Et2O to give 58.5 mg (0.2 mMol, 20%): mp=169°-170° C.

후처리

  1. customto come to ambient temperature
  2. filtrationthe solution filtered
  3. extractionThe aqueous DMAC solution was extracted with Et2O (3×3 mL)
  4. customthe Et2O was evaporated in vacuo to an oil which
  5. washElution
  6. customwith CHCl3MeOH (15:1 v/v), combination of the appropriate fractions and evaporation in vacuo
  7. customyielded an oil which
  8. customwas crystallized from Et2O
  9. customto give 58.5 mg (0.2 mMol, 20%)

출처 및 근거

ORD 기록
ord-d1b2c4078cba42f59a0978528ea2b497
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05064946

연결된 노트

불러오는 중…