HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Triethylamine → (+/-)-{4-Chloro-2-[5-(2-methoxy-benzylthiocarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-4-yl]-phenoxy}-acetic acid
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | Sodium Hydroxide | HCID 14798 | — |
| Edukt | 2-Methoxybenzyl isothiocyanate | HCID 140256 | — |
| Edukt | (+/-)-[4-Chloro-2-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-4-yl)-phenoxy]-acetic acid ethyl ester hydrochloride | HCID 90021828 | — |
| Lösungsmittel | Formic Acid | HCID 284 | — |
| Lösungsmittel | Acetonitrile | HCID 6342 | — |
| Produkt | (+/-)-{4-Chloro-2-[5-(2-methoxy-benzylthiocarbamoyl)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-4-yl]-phenoxy}-acetic acid | HCID 72948702 | — |
Reaktionsschritte
To a solution of (±)-[4-chloro-2-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-4-yl)-phenoxy]-acetic acid ethyl ester hydrochloride (50 mg, 0.13 mmol, 1.00 eq.) and NEt3 (54 μL, 0.39 mmol, 3.00 eq.) in MeCN (1 mL), 2-methoxybenzyl isothiocyanate (24 mg, 0.14 mmol, 1.05 eq.) in MeCN (1 mL) was added. The mixture was stirred at r.t. for 18 hours. 1M aq. NaOH (0.5 mL) was added. The mixture was stirred at r.t. for 18 hours. The solution was neutralized with formic acid, purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions), and concentrated in vacuo to give the desired acid as a white solid.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09169270B2 |
| Quelldatensatz | uspto-grants-2015_10 |
| ORD ID | ord-c0b01d7c0be74736aacdc50b232042f4 |
| Quellennotiz | uspto-grants-2015_10 |