Triethylamine → Daunorubicin

HRID 2248035Notes

Reaction equation

HRID 2248035 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:18]3[C:13](=[C:14]([OH:32])[C:15]4[C:24](=[O:25])[C:23]5[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:22]=5[C:20](=[O:21])[C:16]=4[C:17]=3[OH:19])[CH2:12][C@@:11]([OH:36])([C:33]([CH3:35])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:37])[C@@H:3]1[OH:38].Cl.C(N(CC)CC)C.CC(C)=O.CCOCC>CS(C)=O>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:18]3[C:13](=[C:14]([OH:32])[C:15]4[C:24](=[O:25])[C:23]5[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH3:31])[C:22]=5[C:20](=[O:21])[C:16]=4[C:17]=3[OH:19])[CH2:12][C@@:11]([OH:36])([C:33]([CH3:35])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:37])[C@@H:3]1[OH:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62770Daunorubicin HydrochlorideHCID 21584533Acetone diethylether

Product 1

HCID 30323Daunorubicin

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 0.31 g of polymer precursor (9) (containing 1.35×10-4 mol of ONp groups) in 1.2 ml DMSO was added 0.028 g (5.1×10-5 mol) of daunomycin hydrochloride in 0.1 ml DMSO and 0.0052 g (5×10-5 mol) of triethylamine. The reaction mixture was stirred at room temperature for 60 minutes and then poured into 400 ml of acetone: ether (3:1) mixture to precipitate the polymer. The polymer contained 2.5 mol % of side-chains terminating in daunomycin and 4.3 mol % of side-chains terminating in unreacted ONp groups.

Workup

  1. customto precipitate the polymer
  2. customterminating in daunomycin
  3. custom4.3 mol % of side-chains terminating in unreacted ONp groups

Sources & evidence

ORD record
ord-e2f04dd9b1864b9fa340a4d25a8081ce
Source dataset
uspto-grants-1991_08
Patent number
US05037883

Reaction notes

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