HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → 1-(4-Benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | O-Allylhydroxylamine hydrochloride | HCID 3084724 | — |
| Reactant | 1-(4-Benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid | HCID 18333730 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 1-(4-Benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amide | HCID 54442552 | 102.9% |
Reaction Steps
A solution of 1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid (0.077 g, 0.19 mmol), HOBT (0.044 g, 0.29 mmol), O-allylhydroxylamine hydrochloride (0.043 g, 0.29 mmol), di-isopropylethylamine (0.066 mL, 0.38 mmol) and CH2Cl2 (2 mL) was treated with EDCl (0.056 g, 0.29 mmol). After stirring for 24 h at room temperature, the mixture was diluted with ethyl acetate, washed with 1M HCl, saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated in vacuo, affording 1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amide (0.090 g, 100%) as a colorless syrup:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06329397B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-81bd23a758c640d184d29f6404d11fe4 |
| Source note | uspto-grants-2001_12 |