Mitomycin C → Mitomycin C

HRID 1292718

반응식

HRID 1292718 반응식
[CH3:1][C:2]1[C:8](=[O:9])[C:7]2[N:10]3[C@@:14]([O:21][CH3:22])([C@H:15]([CH2:16][O:17][C:18]([NH2:20])=[O:19])[C:6]=2[C:4](=[O:5])[C:3]=1[NH2:24])[C@H:13]1[NH:23][C@H:12]1[CH2:11]3>CN(C)C=O>[CH3:1][C:2]1[C:8](=[O:9])[C:7]2[N:10]3[C@@:14]([O:21][CH3:22])([C@H:15]([CH2:16][O:17][C:18]([NH2:20])=[O:19])[C:6]=2[C:4](=[O:5])[C:3]=1[NH2:24])[C@H:13]1[NH:23][C@H:12]1[CH2:11]3.[CH3:7][N:10]([C:14]1[CH:15]=[CH:6][CH:4]=[CH:3][N:24]=1)[CH3:11]

참가 물질

4

반응물 1

HCID 5746Mitomycin C

생성물 2

HCID 5746Mitomycin CHCID 218852-Dimethylaminopyridine

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of mitomycin C (MMC, 0.35 mmol), dimethylaminopyridine (0.1 mmol) and dimethylformamide (DMF, 2 mL) was prepared. The MMC solution was slowly added to the acyl chloride solution. After overnight reaction, the methylene chloride was evaporated off and the crude product was recovered by addition of isopropanol followed by filtration. The mPEG-DTB-MMC conjugate was further purified by two precipitation from ethanol. Yield: 3.4 g. The MMC content (≈90%) was determined by UV. The conjugate was further characterized by 1H NMR (360 MHz, CDCl3): δ 1.18 (d, J=7.5, 3H), 1.76 (s, 3H), 2.96–3.03 (m, 3H), 3.19 (s, 3H), 3.29 (dd, J=4.7 and 2.9 Hz, 1H), 3.41 (dd, J=5.0 and 2.2 Hz, 1H), 3.48 (dd, J=13.7 and 2.5 Hz, 1H), 3.60 (s, PEG, 1000H), 4.15 (t, OCOCH2, 2H), 4.27–4.36 (m, 2H), 4.43 (d, J=13.3 Hz, 1H), 4.61 (s, 2H), 4.90 (ddd, J=10.4 and 5.0 and 2.2 Hz, 1H), 5.00 (s, 2H), 7.32 (d, J=8.6 Hz, 2H), 7.50 (d, J=7.9 Hz, 2H).

후처리

  1. customAfter overnight reaction
  2. customthe methylene chloride was evaporated off
  3. customthe crude product was recovered by addition of isopropanol
  4. filtrationfollowed by filtration
  5. customThe mPEG-DTB-MMC conjugate was further purified by two precipitation from ethanol

출처 및 근거

ORD 기록
ord-41075eb82baf41f48ee5c2617b5d4e03
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238368B2

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