Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Diethyl cyanophosphonate | HCID 76257 | — |
| Reactant | 2-(4-((2,4-Dioxothiazolidin-5-YL)methyl)phenoxy)acetic acid | HCID 11323485 | — |
| Reactant | t-Butyl N-[2-amino-5-(4-methoxymethoxy-2,3,5-trimethylphenoxy)phenyl]N-methylcarbamate | HCID 18461355 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 18461441 | HCID 18461441 | 75.9% |
Reaction Steps
7.34 g of diethyl cyanophosphonate were added to a mixture of 18.7 g of t-butyl N-[2-amino-5-(4-methoxymethoxy-2,3,5-trimethylphenoxy)phenyl]-N-methylcarbamate, 12.6 g of 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid, 4.55 g of triethylamine and 300 ml of anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated by evaporation. Water was then added to the concentrate. After extraction with ethyl acetate, the extract was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography through a silica gel column (eluting solvent: n-hexane/ethyl acetate=1/1), whereby 23.1 g of the desired compound were obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06432993B1 |
|---|
| Source dataset | uspto-grants-2002_08 |
|---|
| ORD ID | ord-dcc273650ee24bdc8612371db615b373 |
|---|
| Source note | uspto-grants-2002_08 |
|---|