Triethylamine → Morpholinodoxorubicin

HRID 1758789Notes

Reaction equation

HRID 1758789 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:37])([C:33]([CH2:35][OH:36])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([NH2:38])[C@@H:3]1[OH:39].Cl.I[CH2:42][CH2:43][O:44][CH2:45][CH2:46]I.C(N(CC)CC)C>CN(C=O)C>[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:37])([C:33]([CH2:35][OH:36])=[O:34])[CH2:10]2)[CH2:5][C@H:4]([N:38]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)[C@@H:3]1[OH:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443939Doxorubicin HydrochlorideHCID 34307792-Iodoethyl ether

Product 1

HCID 92398MorpholinodoxorubicinYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of adriamycin hydrochloride (20 mg; 0.034 mmoles) in 1 ml of DMF were added 200 mg (0.614 mmoles) of bis(2-iodoethyl)ether and 0.014 ml (0.104 mmoles) of triethylamine, and the reaction was carried out for 36 hours at room temperature. The product was worked up in the same way as in the purification procedure of Example 1 to give 13 mg (yield 61%) of the title compound.

Workup

  1. customThe product was worked up in the same way as in the purification procedure of Example 1

Sources & evidence

ORD record
ord-9be7040ef0b84ff58f3257fae53e1011
Source dataset
uspto-grants-1983_02
Patent number
US04374980

Reaction notes

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