HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 54559825, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2,2-Diphenylacetyl chloride | HCID 74637 | — |
| Reactant | (2R)-2-amino-5-[(benzyloxy)carbonyl]aminopentanoic acid hydrochloride | HCID 69885572 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 54559825 | HCID 54559825 | 91.2% |
Reaction Steps
1 N NaOH (75 mL) was added to a stirred suspension of (R)-N5 -(Cbz)-ornithine hydrochloride (7.5 g; 25 mmol) in THF (114 mL). Once the starting material had dissolved, diphenylacetyl chloride (6.7 g; 26.3 mmol) was added. The reaction was stirred for 3 h at room temperature, then made acidic with cold 1 N HCl and extracted with EtOAc (3×75 mL). The EtOAc extract was washed with brine, dried with Na2SO4, and concentrated to afford the crude product. Purification by flash chromatography on silica eluting with EtOAc:hexanes (1:1) afforded the sub-title compound (10.5 g; 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06127414 |
| Source dataset | uspto-grants-2000_10 |
| ORD ID | ord-17a7b31f36c146a3a93a681869d39f9a |
| Source note | uspto-grants-2000_10 |