Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Isopropanol | HCID 3776 | — |
| Reactant | erythro-N-Boc-O-benzyl-L-tyrosine epoxide | HCID 2761804 | — |
| Reactant | 1-Aminotetralin, (S)- | HCID 7058074 | — |
| Product | HCID 57512964 | HCID 57512964 | — |
Reaction Steps
A mixture of tert-butyl (1S)-2-[4-(benzyloxy)phenyl]-1-[(2S)-oxiranyl]ethylcarbamate (V, 1.58 g, 4.28 mmol) and 3-methoxybenzylamine (VI, 825 microliter, 6.42 mmol) in isopropanol (45 mL) is heated to 90 degrees C. for 4 hours. Upon cooling to 20-25 degrees C., the reaction mixture is concentrated under reduced pressure. Purification by flash chromatography (silica; methylene chloride/methanol/ammonium hydroxide 98/1/1 to 95/:4/1) gives tert-butyl (1S,2R)-1-[4-(benzyloxy)benzyl]-2-hydroxy-3-[(3-methoxybenzyl)amino]propylcarbamate (VII, 1.97 9), NMR (300 MHz, MeOH-d4): □ 7.41-6.79, 5.05, 4.33-3.33, 3.74, 3.54, 3.03-2.46 and 1.29; ESI-MS (m/z) [M+H]+=507.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07498436B2 |
|---|
| Source dataset | uspto-grants-2009_03 |
|---|
| ORD ID | ord-04d9af13482f4ee0a0c68b6a5023c3fe |
|---|
| Source note | uspto-grants-2009_03 |
|---|
