L-Cysteic acid → Doxorubicin

HRID 1614848Notes

Reaction equation

HRID 1614848 reaction equation
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:14]3=[C:15]([OH:32])[C:16]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][C:26]=5[O:30][CH3:31])[C:20](=[O:21])[C:17]=4[C:18]([OH:19])=[C:13]3[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.[Na].N[C@H](C(O)=O)CS(=O)(O)=O>>[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:14]3=[C:15]([OH:32])[C:16]4[C:28](=[O:29])[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][C:26]=5[O:30][CH3:31])[C:20](=[O:21])[C:17]=4[C:18]([OH:19])=[C:13]3[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]

Participants

4

Reactant 3

HCID 72886L-Cysteic acid2×HCID 443939Doxorubicin HydrochlorideHCID 5360545Sodium2×

Product 1

HCID 31703Doxorubicin

Procedure

50 ml doxorubicin hydrochloride solution (8.6 mg/ml) was added drop-wise under stirring to 200 ml of a solution containing sodium salt of methyl ester of N-all-trans-retinoyl cysteic acid (3 mg/mL) and sodium salt of methyl ester of 13-cis-retinoyl cysteic acid (3 mg/ml) in 500 ml round-bottom flask. Stirring was continued for an additional 20 min. The doxorubicin concentration in the obtained formulation was 1.6 mg/ml. The solution obtained was filtered through 0.2 mm filter and freeze dried. The filtration did not result in reduction of doxorubicin concentration.

Workup

  1. concentrationThe doxorubicin concentration in the obtained formulation
  2. customThe solution obtained
  3. filtrationwas filtered through 0.2 mm
  4. filtrationfilter
  5. customfreeze dried
  6. filtrationThe filtration

Sources & evidence

ORD record
ord-f0917811e57c4986afcf74b3f33aedeb
Source dataset
uspto-grants-2014_07
Patent number
US08765173B2

Reaction notes

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