HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl chloroformate → (3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl chloroformate | HCID 6586 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | {3-[2-(Benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester | HCID 58288498 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester | HCID 58288472 | — |
Reaction Steps
To {3-[2-(benzylamino-methyl)-4-bromo-phenoxy]-phenyl}-acetic acid methyl ester (0.076, 0.17 mmol) and methyl chloroformate (0.01 mL, 0.18 mmol) in CH2Cl2 (2 mL) was added triethylamine (0.02 mL, 0.18 mmol), and the reaction was stirred at room temperature for 3 hours. Some starting material was still observed by analytical LCMS, so additional methyl chloroformate (0.02 mL) and triethylamine (0.03 mL) was added, and the reaction was stirred overnight. The mixture was concentrated and purified by silica gel chromatography (10-30% EtOAc in hexanes) to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08426449B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-537e0e6ff668484faa58e66c9bccbedc |
| Source note | uspto-grants-2013_04 |