Tetrahydrofuran → Isatoic Anhydride

HRID 432012Notes

Reaction equation

HRID 432012 reaction equation
CO[C:3]1[CH:8]=[C:7]2C(N3[C@H](C=[N:17][C:6]2=[CH:5][C:4]=1O)CCC3)=O.ClC(Cl)(O[C:23](=[O:29])[O:24][C:25](Cl)(Cl)Cl)Cl.C1C[O:34]CC1>>[C:5]12[C:6](=[CH:7][CH:8]=[CH:3][CH:4]=1)[NH:17][C:25](=[O:34])[O:24][C:23]2=[O:29]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 94429TriphosgeneHCID 1110762681307-24-6

Product 1

HCID 8359Isatoic Anhydride

Procedure

This invention provides a very short route for efficient synthesis of PBD analogues, e.g. DC-81. The synthesis starts with the reaction of a substituted 2-amino benzoic acid with triphosgene in THF under reflux to form an isatoic anhydride compound, which is subsequently coupled with a substituted or unsubstituted L-proline compound in DMSO to produce a dilactam compound, followed by reaction with MOMCl. The resulting compound is then subjected to a reduction reaction in the presence of lithium borohydride (LiBH4).

Workup

  1. customThis invention provides a very short route
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-c14be0f2591f4738a84ae7f10011a36b
Source dataset
uspto-grants-2003_12
Patent number
US06660856B2

Reaction notes

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