HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphate → (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylic Acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosphate | HCID 1061 | — |
| Reactant | 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylate | HCID 131722901 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylic Acid | HCID 20698522 | 0.8% |
Reaction Steps
To a solution of 4.70 g of 4-nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 10 ml of THF and 10 ml of {fraction (1/15)} M phosphate buffer was added 240 mg of 10% Pd-C. The reactor was purged with hydrogen, and the reaction mixture was stirred at room temperature for 3 hours. The catalyst was collected by filtration and washed with water. The filtrate was washed with ethyl acetate, and the aqueous layer was purified by column chromatography on DIAION HP-20 to give 27.5 mg of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06310056B1 |
| Source dataset | uspto-grants-2001_10 |
| ORD ID | ord-c3eb59ce70ca4e6690f321e5d6b3c451 |
| Source note | uspto-grants-2001_10 |