Chloroform → [(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18R,19Z,21Z)-2,15,17,29-tetrahydroxy-18-(hydroxymethyl)-11-methoxy-3,7,12,14,16,22-hexamethyl-6,23,26,27-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29)-heptaen-13-yl] acetate

HRID 648191Notes

Reaction equation

HRID 648191 reaction equation
[CH3:1][C@@H:2]1[C@H:35]([OH:36])[C@@H:34]([CH3:37])[C@@H:33]([OH:38])[C@@H:32]([CH3:39])[C@H:31]([O:40][C:41]([CH3:43])=[O:42])[C@H:30]([CH3:44])[C@@H:29]([O:45][CH3:46])[CH:28]=[CH:27][O:26][C@@:24]2([CH3:47])[O:25][C:15]3[C:16]([C:22]2=[O:23])=[C:17]2[C:18]([C:20](=[O:21])[C:10](=[C:11]([OH:50])[C:12]2=[C:13]([OH:49])[C:14]=3[CH3:48])[NH:9][C:7](=[O:8])[C:6]([CH3:51])=[CH:5][CH:4]=[CH:3]1)=[O:19].C(Cl)(Cl)Cl.C(OCC)(=[O:58])C>CO.CC(C)=O.C1(C)C=CC=CC=1.O>[CH3:44][C@H:30]1[C@@H:31]([O:40][C:41]([CH3:43])=[O:42])[C@H:32]([CH3:39])[C@H:33]([OH:38])[C@H:34]([CH3:37])[C@@H:35]([OH:36])[C@@H:2]([CH2:1][OH:58])[CH:3]=[CH:4][CH:5]=[C:6]([CH3:51])[C:7](=[O:8])[NH:9][C:10]2[C:20]([C:18](=[O:19])[C:17]3[C:12]([C:11]=2[OH:50])=[C:13]([OH:49])[C:14]([CH3:48])=[C:15]2[O:25][C@@:24]([CH3:47])([C:22]([C:16]=32)=[O:23])[O:26][CH:27]=[CH:28][C@@H:29]1[O:45][CH3:46])=[O:21]

Participants

8

Reactant 3

HCID 6212ChloroformHCID 8857Ethyl AcetateHCID 102115525[(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,26,27-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29)-heptaen-13-yl] acetate

Product 1

HCID 102115528[(7S,9Z,11S,12R,13S,14R,15R,16R,17S,18R,19Z,21Z)-2,15,17,29-tetrahydroxy-18-(hydroxymethyl)-11-methoxy-3,7,12,14,16,22-hexamethyl-6,23,26,27-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29)-heptaen-13-yl] acetate

Reagents, catalysts & solvents 4

HCID 180AcetoneSolvent2×HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In order to manufacture small quantities of 3-hydroxyrifamycin S in pure form, it is advantageous to use preparative thin-layer chromatography; suitable eluants for this purpose are, for example, silica gel thin-layer plates (like the above-mentioned plates P 254) and a mixture of chloroform and methanol (4:1 or 6:1), or of ethyl acetate, acetone and water (72:24:4) or of toluene, acetone and methanol (5:3:2). 3,31-Dihydroxyrifamycin S and 1-desoxy-1-oxarifamycin S are obtained in pure form in an analogous manner using the same plates and elution systems. The desired zone is separated off mechanically, collected and extracted with a suitable solvent, preferably ethyl acetate, in order to isolate the pure product. If necessary, this purification process can be repeated using various adsorbents and/or solvent combinations.

Sources & evidence

ORD record
ord-d12b92df621a43368431ffff0d577063
Source dataset
uspto-grants-1983_10
Patent number
US04411896

Reaction notes

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