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

HRID 1885527

반응식

HRID 1885527 반응식
[N:1]([C@@:4]1(O)[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:21]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:21])[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 70297m-Chloroperbenzoic acidHCID 544067393'-Azido-2'-deoxyuridine

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매2회

실험 절차

3'-Azido-2'-deoxyuridine (0.25 g; 1 mMol) was dissolved in 2 mL dry dimethylacetamide (DMAC), cooled to 0° 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 CHCl3 /MeoH (15:1 v/v), combination of 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.; UV (nm): at pH 1 max=276 (=7400), min=239 (=500); at pH 13 max=274 (=6400), min=249 (=3800); H1NMR (DMSO-d6) 8.29 (s, 1H, H6), 6.05 (t,1H,H1', J=5.5 Hz), 5.49-5.29 (m,1H,5'-OH), 4.44-4.20 (m,1H,H3'), 3.88-3.71 (m,1H,H4'), 3.71-3.53 (m,2H,H5'), 2.63-2.31 (m,2H,H2'); analysis calculated for C9H10N5O4Cl:ε37.58, H 3.50, N 24.35, Cl 12.32.

후처리

  1. temperaturecooled to 0°
  2. customto come to ambient temperature
  3. filtrationthe solution filtered
  4. extractionThe aqueous DMAC solution was extracted with Et2O (3×3 mL)
  5. customthe Et2O was evaporated in vacuo to an oil which
  6. washElution
  7. customwith CHCl3 /MeoH (15:1 v/v), combination of appropriate fractions and evaporation in vacuo
  8. customyielded an oil which
  9. customwas crystallized from Et2O
  10. customto give 58.5 mg (0.2 mMol, 20%)

출처 및 근거

ORD 기록
ord-e31d215dcac14fa6912b06f52715dc51
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05145840

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