HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (S)-(1-(2-amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | (S)-(1-(2-(tert-butoxycarbonyl)amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamate | HCID 59778634 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | (S)-(1-(2-amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamate | HCID 59778460 | 106.1% |
Reaction Steps
To a solution of (S)-(1-(2-(tert-butoxycarbonyl)amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamate (145 mg, 0.22 mmol) in CH3OH (1 mL) was added 4M HCl in dioxane (200 μL, 0.8 mmol, 3.6 equiv.), which was stirred for 2 h. The reaction mixture was concentrated to dryness by co-evaporating with toluene to give (S)-(1-(2-amino-3-hydroxypropanoyl)-4-(2-chlorobenzylcarbamoyl)piperidin-4-yl)methyl 4-(trifluoromethyl)phenylcarbamate (130 mg, quant.). LRMS (M+H+) m/z 557.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08071625B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-91699c7b1afb42c8a27ef0375b959929 |
| Source note | uspto-grants-2011_12 |