HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanamine, N-methoxy-, hydrochloride (1:1) → 2-(N-Boc)amino-3-(4-cyanophenyl)-N-methoxy-N-methylpropanamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanamine, N-methoxy-, hydrochloride (1:1) | HCID 81138 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | N-(tert-Butoxycarbonyl)-4-cyano-L-phenylalanine | HCID 7020841 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-(N-Boc)amino-3-(4-cyanophenyl)-N-methoxy-N-methylpropanamide | HCID 21070238 | — |
Reaction Steps
2 g of (N-Boc)-4-cyanophenylalanine, 2.32 g of TBTU, 2.40 ml of DIPEA and 806 mg of N,O-dimethylhydroxylamine hydrochloride are mixed together in 30 ml of DCM. After stirring for 24 hours at RT, the reaction mixture is concentrated to dryness and the residue is then extracted with EtOAc. The organic phase is washed with a pH 2 buffer solution, a saturated NaHCO3 solution and then a saturated NaCl solution. The expected compound crystallizes from a mixture of isopropyl ether and pentane (1.89 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07157454B2 |
| Source dataset | uspto-grants-2007_01 |
| ORD ID | ord-90a6d7c751cc4148b1a4a3cdbb4e6014 |
| Source note | uspto-grants-2007_01 |