Chloroform → HCID 101636766, compound

HRID 649126Notes

Reaction equation

HRID 649126 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:41](=[O:42])[C:36]3=[C:37]([Cl:40])[C:38](=[O:39])[C:5]2=[C:6]([C:9]([C:11]([CH3:51])=[CH:12][C@H:13]([CH3:50])[C@@H:14]([OH:49])[C@@H:15]([CH3:48])[CH:16]=[CH:17][C@@H:18]([OH:47])[CH2:19][CH:20]=[C:21]([CH3:46])[C:22]([CH2:24][C@H:25]([OH:45])[C@@H:26]([CH3:44])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=[C:32](C)[C:33]([NH:35]3)=[O:34])=[O:23])=[O:10])[C:7]=1[OH:8].C(Cl)(Cl)Cl>CO>[CH3:44][C@@H:26]1[C@@H:25]([OH:45])[CH2:24][C:22](=[O:23])[C:21]([CH3:46])=[CH:20][CH2:19][C@H:18]([OH:47])[CH:17]=[CH:16][C@H:15]([CH3:48])[C@H:14]([OH:49])[C@@H:13]([CH3:50])[CH:12]=[C:11]([CH3:51])[C:9](=[O:10])[C:6]2[C:7]([OH:8])=[C:2]([CH3:1])[CH:3]=[C:4]3[C:41](=[O:42])[C:36](=[C:37]([Cl:40])[C:38]([C:5]=23)=[O:39])[NH:35][C:33](=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=[CH:27]1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 10101379HCID 10101379, compound

Product 1

HCID 101636766HCID 101636766, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

36 g of crude extract were applied to a 3.5×49 cm silica gel column, and eluted successively with chloroform and a chloroform:methanol mixture in which the methanol concentration gradually rose to 5% (final composition 95:5). In this way, 14.6 g of semi-pure compound were obtained, and this was applied to a silica gel (200-300 mesh) column 6×31 cm in size, and was then eluted with a benzene:ethyl acetate mixture gradually increasing the ethyl acetate concentration to 60% (final composition 4:6). This resulted in fraction A in an amount of about 0.19 g and fraction B in an amount of about 1.2 g. For further purification, fraction A was applied to a 1.4×80 cm Sephadex LH 20® column and was eluted with methanol, resulting in 142 mg of a compound which was purified by preparative thin-layer chromatography (silica gel plates of thickness 0.5 mm) in a mixture of chloroform:methanol (95:5). This resulted in 96 mg of a pure compound which was identified as the known antibiotic naphthomycin A. Then a 6×30 cm silica gel H® column (without binder) was charged, as a chromatography column, with fraction B, and elution was carried out with a mixture of chloroform and methanol (96:4). This resulted in 650 mg of a semi-pure substance which was purified by a preparative thin-layer chromatography (silica gel plates 1 mm thick) in a mixture of chloroform and methanol (95:5), and was then recrystallized from a petroleum ether:benzene:ethyl acetate mixture, this resulting in naphthomycin H in an amount of 120 mg.

Workup

  1. additionThen a 6×30 cm silica gel H® column (without binder) was charged, as a chromatography column, with fraction B, and elution
  2. customThis resulted in 650 mg of a semi-pure substance which
  3. customwas purified by a preparative thin-layer chromatography (silica gel plates 1 mm thick) in a mixture of chloroform and methanol (95:5)
  4. customwas then recrystallized from a petroleum ether

Sources & evidence

ORD record
ord-207f42f6c1ac491b90fa0d1fb61d98b9
Source dataset
uspto-grants-1988_04
Patent number
US04738958

Reaction notes

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