HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 3-[(3-Chloro-5-methoxy-benzoyl)-isopropyl-amino]-propionic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | Methyl 3-[(propan-2-yl)amino]propanoate | HCID 12774812 | — |
| Reactant | 3-Chloro-5-methoxybenzoic acid | HCID 12909341 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-[(3-Chloro-5-methoxy-benzoyl)-isopropyl-amino]-propionic acid methyl ester | HCID 69948825 | 102.1% |
Reaction Steps
To a stirred solution of 3-chloro-5-methoxy-benzoic acid (0.932 g), TBTU (3.21 g) and in DMF (10 ml) was added DIPEA (1.73 ml) followed by 3-isopropylamino propionic acid methyl ester (0.871 g) after 10 min. The reaction mixture was stirred at room temperature for 48 h and then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water. The organic phase was washed with further water and 2M aqueous sodium hydroxide, water and dried with brine and over sodium sulphate and concentrated under reduced pressure to give the title compound as a brown oil (1.6 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06326386B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-dc6c1c94c12141539f7f9e9ad0967479 |
| Source note | uspto-grants-2001_12 |