Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | Tris(4-chlorophenyl)phosphine | HCID 70874 | — |
| Reactant | 4-(Dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid | HCID 54671203 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Rhodium | HCID 23948 | — |
| Product | Sulfosalicylic Acid | HCID 7322 | — |
| Product | 4-(Dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-3,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboximidic acid | HCID 54671203 | — |
Reaction Steps
A Parr bottle is charged with 5% rhodium-on-carbon (2.88 gms., 50% wet material; 0.70 mM of rhodium), tri-(4-chlorophenyl)phosphine (0.76 gms., 2.1 mM) in 13 cc. methanol. The mixture is shaken for a half-hour at 62°C., under nitrogen atmosphere, at the end of which time a solution of 3.39 gms., 7.0 mM, of 6-deoxy-6-demethyl-6-methylene-5-hydroxytetracycline hydrochloride in 37 cc. of methanol, containing 7.0 mM of p-toluenesulfonic acid, is added. The bottle is then filled with hydrogen at 50 p.s.i. and shaken overnight at 75°C. for 18 hours. High pressure liquid chromatography of the reaction mixture indicates the presence of 80% α-6-deoxy-5-hydroxytetracycline and 1.5% 6β-epimer. α-6-deoxy-5-hydroxytetracycline may be isolated in 78% yield as the 5-sulfosalicyclic acid salt.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US03954862 |
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| Source dataset | uspto-grants-1976_05 |
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| ORD ID | ord-141ff0ebb7574873878f82ca2b74959c |
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| Source note | uspto-grants-1976_05 |
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