HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 4-Methoxybenzyl (6R,7R)-7-Amino-3-((R)-tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | 2-Bromo-1-[(2R)-tetrahydro-2-furanyl]-ethanone | HCID 11194867 | — |
| Reactant | 4-Methoxybenzyl (RS)-2-hydroxy-2-[(lR,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0)hept-2-en-7-on-6-yl]acetate | HCID 53656123 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-Methoxybenzyl (6R,7R)-7-Amino-3-((R)-tetrahydrofuran-2-yl)ceph-3-em-4-carboxylate | HCID 53841027 | — |
Reaction Steps
4-Methoxybenzyl (RS)-2-hydroxy-2-[(1R,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-on-6-yl]acetate (4.103g) in dichloromethane (15ml) and acetone (15ml) was ring opened with 4-toluenesulphonic acid hydrate (3.33g) in water (8ml) and coupled to (R)-2-bromoacetyltetrahydrofuran (2.11g) in acetone (20ml) with potassium carbonate (0.687g) as described in Example 6(b) for the diastereoisomeric mixture. After purification by flash chromatography, the title compound was obtained as a yellow gum (2.618g, 49%); [α]D -10.7 (c 1.00 CHCl3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06020329 |
| Source dataset | uspto-grants-2000_02 |
| ORD ID | ord-24bb69f6ad8d4a45a71b0f4717ca621d |
| Source note | uspto-grants-2000_02 |