HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → Methyl (2R)-3-{[4-({3-cyclohexyl-5-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-1-YL}methyl)benzoyl]amino}-2-hydroxypropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 4-((3-cyclohexyl-5-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-1-yl)methyl)benzoic acid | HCID 53323247 | — |
| Reactant | (R)-methyl 3-amino-2-hydroxypropanoate hydrochloride | HCID 86590828 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl (2R)-3-{[4-({3-cyclohexyl-5-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-1-YL}methyl)benzoyl]amino}-2-hydroxypropanoate | HCID 57801615 | — |
Reaction Steps
A solution of 24.6 mg product from Step A Example 6, 15.9 mg EDC, 11.2 mg HOBt, 17.2 mg methyl (2R)-3-amino-2-hydroxypropanoate hydrochloride from Step C Example 4 and 39 μL DIEA in 0.5 mL DMF was stirred at room temperature over night. The title compound was isolated by preparative HPLC using 55˜75% MeCN gradient over 10 minutes at 8.0 mL per minute with 0.1% TFA on a 9.4×250 mm SB-C18 Zorbax column as a white solid after lyophilization. LC-MS: 2.55 min. (M+H=546.3).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07989475B2 |
| Source dataset | uspto-grants-2011_08 |
| ORD ID | ord-83da0f91451b4b8a8636bbefc1080c82 |
| Source note | uspto-grants-2011_08 |