HuagongsheHuagongshe Chemistry Print Report · For research reference only
L-Hydroxyproline → 4-Hydroxy-L-proline methyl ester hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | L-Hydroxyproline | HCID 5810 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 4-Hydroxy-L-proline methyl ester hydrochloride | HCID 11435319 | 88.2% |
Reaction Steps
To a suspension of trans-4-hydroxy-L-proline (200 g: 1.525 mole) in methanol (800 ml), acetylchloride (163 ml: 2.288 mole) is added dropwise under ice cooling in a nitrogen atmosphere. The mixture is warmed to room temperature, mixed with thionyl chloride (55.7 ml: 0.763 mole), and stirred for 4 hours at 40° C. to give (2S,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride (244.27 g). Yield: 88%. Colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05703243 |
| Source dataset | uspto-grants-1997_12 |
| ORD ID | ord-d1af03d4baa04b4aa6b367c888c1f6e2 |
| Source note | uspto-grants-1997_12 |