HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 11397615, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | tert-butyl N-(2-hydroxyethyl)carbamate | HCID 2733206 | — |
| Reactant | HCID 68871617 | HCID 68871617 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 11397615 | HCID 11397615 | 16% |
Reaction Steps
Triphenylphosphine (260 mg, 1.0 mmol) was added to a solution of the product from Step 5 (220 mg, 0.5 mmol) and N—BOC-ethanolamine (161 mg, 1.0 mmol) in dioxane (4 mL) followed by addition of di-isopropylazodicarboxylate (197 uL, 1.0 mmol) and the resulting solution was allowed to stir at rt overnight. The reaction mixture was poured into water and extracted with EtOAc. The organic phases were combined, washed with brine, dried (MgSO4), filtered and the filtrate concentrated. The crude material was dissolved in dichloromethane (2 mL) and treated with TFA (1 mL) for 30 min, then concentrated and the residue was purified by reverse phase HPLC to give the title compound (38 mg, 16%). MS (ES+) m/e 487 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07547779B2 |
| Source dataset | uspto-grants-2009_06 |
| ORD ID | ord-845df6269aa14ad583ad318eba60a5b5 |
| Source note | uspto-grants-2009_06 |