HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carbonyl-2(S)-phenylsulfonylamino-beta-alanine methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carboxylic acid | HCID 19068150 | — |
| Reactant | Methyl 3-Amino-2(S)-phenylsulfonylaminopropionate hydrochloride | HCID 22865877 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-[4-(N-BOC-Piperidin-4-yl)butyloxy]isoxazole-5-carbonyl-2(S)-phenylsulfonylamino-beta-alanine methyl ester | HCID 86752945 | 72.3% |
Reaction Steps
A stirred mixture of 4-5 (147 mg, 0.4 mmol), 2-9a (149 mg, 0.4 mmol), HOBT (61 mg, 0.4 mmol), DIEA (215 μL, 1.2 mmol), and DMF (6 mL) at -15° C. was treated with EDC (77 mg, 0.4 mL) followed by removal of the cooling bath. After 72 h, the reaction mixture was diluted with EtOAc and then washed with 1M NaHSO4 and brine, dried (MgSO4), and concentrated. Flash chromatography (silica, 10% acetone/CH2Cl2) gave 4-6 (176 mg) as a viscous oil. Rf 0.24 (silica, 10% acetone/CH2Cl2).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05786373 |
| Source dataset | uspto-grants-1998_07 |
| ORD ID | ord-c675be25555043648775db5039eeaa6b |
| Source note | uspto-grants-1998_07 |