HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → N-[(Benzyloxy)carbonyl]-O-(trifluoromethyl)-L-tyrosine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | (S)-2-Amino-3-(4-(trifluoromethoxy)phenyl)propanoic acid hydrochloride | HCID 69017088 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | N-[(Benzyloxy)carbonyl]-O-(trifluoromethyl)-L-tyrosine | HCID 69017443 | — |
Reaction Steps
(2S)-2-Amino-3-[4-(trifluoromethoxy)phenyl]propanoic acid hydrochloride (3 mg) prepared in Reference Example 3 (3b) was dissolved in 0.5 N sodium hydroxide (100 μL), and then (benzyloxy)carbonyl chloride (ZCl, 5 μL) was added thereto. The resulting mixture was stirred, and then water (100 μL) was added thereto. The resulting mixture was changed to acidic with 1 N hydrochloric acid (50 μL) and extracted with ethyl acetate (300 μL) to obtain the corresponding (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[4-(trifluoromethoxy)phenyl]propanoic acid. The optical purity was determined by HPLC under the following conditions.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08344029B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-447ef25ddde94896b942df72d3f249ab |
| Source note | uspto-grants-2013_01 |