HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-Methylmorpholine → N-[2(R,S)-Acetylthiomethyl-3-phenylpropanoyl]-(S)-isoserine benzyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 2-[(Acetylthio)methyl]-3-phenylpropionic Acid | HCID 9991796 | — |
| Reactant | benzyl (2S)-3-amino-2-hydroxypropanoate hydrochloride | HCID 131717979 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | N-[2(R,S)-Acetylthiomethyl-3-phenylpropanoyl]-(S)-isoserine benzyl ester | HCID 131717981 | — |
Reaction Steps
Add 2(R,S)-acetylthiomethyl-3-phenylpropionic acid (0.59 g) to (S)-isoserine benzyl ester, hydrochloride (0.578 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (0.53 g), 1-hydroxybenzotriazole (HOBT) (0.37 g) and N-methylmorpholine (0.80 ml) in dimethylformamide (DMF) (10 ml), and stir the resulting mixture for 20 hours. Concentrate the reaction mixture in vacuo and partition the residue between dichloromethane/water. Concentrate the dried (MgSO4) dichloromethane solution in vacuo. Chromatograph the resulting residue on a column of silica gel (1 L) using chloroform:methanol 19.5:1 as eluant to give the title compound, a colorless oil, [α]D26 =+12.3° (MeOH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05219886 |
| Source dataset | uspto-grants-1993_06 |
| ORD ID | ord-94ea739745a14c60a62f47c9d46ab26b |
| Source note | uspto-grants-1993_06 |