Mitomycin C → Mitomycin C

HRID 1292718Notes

Reaction equation

HRID 1292718 reaction equation
[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]

Participants

4

Reactant 1

HCID 5746Mitomycin C

Product 2

HCID 5746Mitomycin CHCID 218852-Dimethylaminopyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-41075eb82baf41f48ee5c2617b5d4e03
Source dataset
uspto-grants-2007_07
Patent number
US07238368B2

Reaction notes

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