HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → {3-[1-[tert-Butoxycarbonyl-(2-methoxy-ethyl)-amino]-2-(tert-butyl-dimethyl-silanyloxy)ethyl]-phenyl}-carbamic acid benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | {3-[2-(tert-Butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethylamino)-ethyl]-phenyl}-carbamic acid benzyl ester | HCID 67329562 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | {3-[1-[tert-Butoxycarbonyl-(2-methoxy-ethyl)-amino]-2-(tert-butyl-dimethyl-silanyloxy)ethyl]-phenyl}-carbamic acid benzyl ester | HCID 67329507 | 32.8% |
Reaction Conditions
| Temperature | 0 °C |
|---|
Reaction Steps
{3-[2-(tert-Butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethylamino)-ethyl]-phenyl}-carbamic acid benzyl ester (1 g) was dissolved in dry DCM (10 mL) and stirred under argon at 0° C. Triethylamine (0.4 g) and (BOC)2O (0.52 g) were added and the reaction mixture was stirred at room temperature for 2 days. The reaction was quenched by addition of water and the mixture extracted with DCM. The organic phase was separated, dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography to give the title compound (400 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08207167B2 |
| Source dataset | uspto-grants-2012_06 |
| ORD ID | ord-4ded7f318f4b4698985b135ca87c0d50 |
| Source note | uspto-grants-2012_06 |