HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 1-(6-amino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosylamino]-1,3-dideoxy-beta-D-ribofuranuronate → 3-{2-Amino-3-[4-(carboxymethoxy)phenyl]propanoylamino}-5-(6-aminopurin-9-yl)-4-hydroxyoxolane-2-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 1-(6-amino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyrosylamino]-1,3-dideoxy-beta-D-ribofuranuronate | HCID 70465257 | — |
| Solvent | Formic Acid | HCID 284 | — |
| Product | 3-{2-Amino-3-[4-(carboxymethoxy)phenyl]propanoylamino}-5-(6-aminopurin-9-yl)-4-hydroxyoxolane-2-carboxylic acid | HCID 476139 | 78.5% |
Reaction Steps
A mixture of methyl 1-(6-amino-9H-purin-9-yl)-3-(N-tert-butoxycarbonyl-O-methoxycarbonylmethyl-L-tyroylamino)-1,3-dideoxy-β-D-ribofuranuronate (200 mg) prepared in Example 76 and formic acid (3 ml) was stirred for 3 hours at room temperature and evaporated to dryness. To the residue was added 1N aqueous sodium hydroxide to adjust the resulting solution to pH 7 and a further 1N aqueous sodium hydroxide (3 ml) was added thereto. The mixture was stirred for 15 minutes at room temperature and adjusted to pH 2 with 1N hydrochloric acid. The resulting precipitates were filtered, washed with water and dried to give 1-(6-amino-9H-purin-9-yl)-3-(O-carboxymethyl-L-tyrosylamino)-1,3-dideoxy-β-D-ribofuranuronic acid (125 mg), mp. 209°-212° C. (dec.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04479942 |
| Source dataset | uspto-grants-1984_10 |
| ORD ID | ord-3f752606371d424eb9883cd1d5cae6f7 |
| Source note | uspto-grants-1984_10 |