Mitomycin C → Mitomycin C

HRID 1292718

反応式

HRID 1292718 の反応式
[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]

参加物

4

反応物 1

HCID 5746Mitomycin C

生成物 2

HCID 5746Mitomycin CHCID 218852-Dimethylaminopyridine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-41075eb82baf41f48ee5c2617b5d4e03
出典データセット
uspto-grants-2007_07
特許番号
US07238368B2

関連ノート

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