HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → N-(1-Methoxycarbonyl-3-methylthiopropyl)-alanyl-L-proline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | methyl (2S)-2-amino-4-(methylsulfanyl)butanoate | HCID 64684 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | (S)-1-(2-Oxopropanoyl)pyrrolidine-2-carboxylic acid | HCID 10130260 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | N-(1-Methoxycarbonyl-3-methylthiopropyl)-alanyl-L-proline | HCID 54124052 | 24.1% |
Reaction Steps
A solution of pyruvoyl-L-proline (185 mg), L-methionine methyl ester (600 mg), and sodium cyanoborohydride (200 mg) in 20 ml of methanol is adjusted to neutrality with dilute methanolic sodium hydroxide. After standing at room temperature for three days the product is absorbed on strong acid ion-exchange resin and eluted with 2% pyridine in water to yield 80 mg of product. The nmr spectrum shows OCH3 at 3.95δ, S-CH3 at 2.2δ and CH-CH3 at 1.55 and 1.7δ. The mass spectrogram on silylated material shows the expected molecular ion at 404 m/e.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04472380 |
| Source dataset | uspto-grants-1984_09 |
| ORD ID | ord-435595efafa6448d80650cb0b7533bb6 |
| Source note | uspto-grants-1984_09 |