Reaction #991793

ord-0ecf59725b2b46b29e17cb5bd3d85d29

Reaction equation

COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
Doxorubicin
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
Doxorubicin hydrochloride
O=P1(N(CCCl)CCCl)NCCCO1
cyclophosphamide
→
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.O=P1(N(CCCl)CCCl)NCCCO1
Cyclophosphamide Doxorubicin

Reactants

COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
Doxorubicin
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl
Doxorubicin hydrochloride
O=P1(N(CCCl)CCCl)NCCCO1
cyclophosphamide

Reagents

None

Solvents

ClC(Cl)Cl
chloroform

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwere added
  2. 2
    workup.ADDITIONfilled with pebbles
  3. 3
    Otherto give two samples of average particle sizes of 250-425μ and 150-250μ

Procedure

To a dark orange solution of Doxorubicin (0.036 g), prepared from Doxorubicin hydrochloride as described in the previous experiment, in chloroform (100 ml) were added while stirring at 50° PLA (4.048 g), cis-Pta2Cl2 (0.495 g) and cyclophosphamide (0.381 g in 40 ml dichloromethane). The mixture was transferred to a 500 ml ball mill jar about one-third filled with pebbles, rotated overnight and worked up as reported in Example 1 to give two samples of average particle sizes of 250-425μ and 150-250μ.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04419340uspto-grants-1983_12