Stavudine → HCID 11722976, 화합물

HRID 988752

반응식

HRID 988752 반응식
[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[CH:12]=[CH:11]2)[CH:3]=1>CN(C)C(=O)C>[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=[O:6])[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[CH:12]=[CH:11]2)[CH:3]=1.[CH3:11][C:10]([N:4]([CH3:5])[CH3:3])=[O:14]

참가 물질

3

반응물 1

HCID 18283Stavudine

생성물 1

HCID 11722976HCID 11722976, 화합물수율 157.7%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
77.5 °C

실험 절차

Crude slightly beige Stavudine (15.9 g, 92.03% pure, 0.0653 mole) was combined with N,N-dimethylacetamide (23.86 g, 1.5 parts) and heated to 75-80° C. when all solids had dissolved. Heating was stopped and the solution was allowed to cool on its own and within minutes crystals began to form. The mixture was further cooled to 0-50° C. and maintained for 2.5 hours. The crystals were filtered, washed with acetone (2×8 mL) and dried to give white Stavudine-DMA solvate (16.04 g, 0.0515 mole, 78.9%) with a chromatographic purity of 99.59%. Since a filtration step was not employed above, when isolating pure stavudine a filtration step would have to be introduced. A further purified Stavudine.DMA solvate had an HPLC purity of 99.98% and the following characterization. The melting point was 132.4-134.8° C. The optical rotation [α]D25=−31.2°. Analyzed for C14H21N3O5 (MW=311.33): C;54.01; H,6.80; N;13:50 Found: C, 53.96; H,6.76; N,13.35. The 300 MHz 1HNMR in DMSO-d6 showed. δ1.74 (s, 3H, Stavudine-CH3); 1.97 (s,3H, CH3); 2.80 and 2.95 (2×s, 2×3H, N(CH3)2); 3.61 (m,2H, 2×H-5′); 4.78 (s, 1H,H-4′); 6.80 (t, 1H, 2×J=1.4, H-2′); 7.66 (s, 1H, H-6); 11.30 (s, 1H, NH). The Stavudine portion of the above spectrum agrees with the literature values (J. Med, Chem, 32, 461 (1989))

후처리

  1. dissolutionhad dissolved
  2. temperatureHeating
  3. temperatureto cool on its own
  4. waitwithin minutes crystals began
  5. customto form
  6. temperatureThe mixture was further cooled to 0-50° C.
  7. temperaturemaintained for 2.5 hours
  8. filtrationThe crystals were filtered
  9. washwashed with acetone (2×8 mL)
  10. customdried

출처 및 근거

ORD 기록
ord-f328d55cc1534dc7b350094e12a169fe
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06635753B1

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