HuagongsheHuagongshe Chemistry Print Report · For research reference only
L-Hydroxyproline → (2R,11aS)-6-chloro-1,2,3,11a-tetrahydro-2-hydroxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | L-Hydroxyproline | HCID 5810 | — |
| Reactant | 5-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione | HCID 639058 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | (2R,11aS)-6-chloro-1,2,3,11a-tetrahydro-2-hydroxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione | HCID 53899318 | — |
Reaction Steps
37.0 g (187.3 mmol) of 6-chloroisatoic acid anhydride and 24.6 g (187.3 mmol) of L-4-hydroxyproline in 180 ml of dimethyl sulphoxide is heated to 100° for 2 hours, evaporated to dryness in a high vacuum and the residue obtained is heated to 130° for 2 hours. By recrystallization from ethanol there is obtained (2R,11aS)-6-chloro-1,2,3,11a-tetrahydro-2-hydroxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione of melting point 284°-287°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04353827 |
| Source dataset | uspto-grants-1982_10 |
| ORD ID | ord-367ff24251fb4fc488f0ead78d9b8186 |
| Source note | uspto-grants-1982_10 |