HCID 178419307, compound → HCID 178519953, compound

HRID 128601Notes

Reaction equation

HRID 128601 reaction equation
C1C(Br)=CC2NC=C(C3N=C(C4C5C=CC(Br)=CC=5NC=4)NC=3)C=2C=1.C1C=CC2NC=C(C3N=C([C:40]4[C:44]5[CH:45]=[CH:46][C:47]([Br:49])=[CH:48][C:43]=5[NH:42][CH:41]=4)NC=3)C=2C=1.C1C=CC2NC=C([C:59]3[N:63]=[C:62]([C:64]([C:66]4[C:70]5[CH:71]=[CH:72][C:73]([OH:75])=[CH:74][C:69]=5[NH:68][CH:67]=4)=[O:65])[NH:61][CH:60]=3)C=2C=1>CCCCCCC.C(OCC)(=O)C.CO.O>[CH:72]1[C:73]([OH:75])=[CH:74][C:69]2[NH:68][CH:67]=[C:66]([C:64]([C:62]3[NH:61][CH:60]=[C:59]([C:40]4[C:44]5[CH:45]=[CH:46][C:47]([Br:49])=[CH:48][C:43]=5[NH:42][CH:41]=4)[N:63]=3)=[O:65])[C:70]=2[CH:71]=1

Participants

5

Reactant 3

HCID 178419307HCID 178419307, compoundHCID 178419308HCID 178419308, compoundHCID 178519954HCID 178519954, compound

Product 1

HCID 178519953HCID 178519953, compound

Reagents, catalysts & solvents 1

HCID 86744338HCID 86744338, compoundSolvent

Procedure

This solid was further fractionated by using centrifugal countercurrent chromatography with two different solvent systems consisting of heptane/ethyl acetate/methanol/water in ratios of 4:7:4:3 and 5:7:4:3. A fraction containing nortopsentin A and a mixture of nortopsentin B and C along with topsentin (400 mg) and bromotopsentin (540 mg) were obtained. Nortopsentin A (250 mg) was purified by HPLC on a Hibar NH2 column (10×250 mm), using 5:1 chloroform/methanol as eluant. Preparative TLC (Kieselgel 60F264, 2 mm thickness, ethyl acetate) afforded a pure nortopsentin C (200 mg) and a fraction containing nortopsentin B. Pure nortopsentin B (250 mg) was finally recrystallized from ethyl acetate/chloroform.

Sources & evidence

ORD record
ord-462b9b35694046849dddc5d7720ebead
Source dataset
uspto-grants-1995_11
Patent number
US05464835

Reaction notes

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