HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2S,4R)-2-((1S 2R)1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert.butyl ester → (1S,2R)-1-[(2S,4R)-(4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-2-vinyl-cyclopropanecarboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2S,4R)-2-((1S 2R)1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert.butyl ester | HCID 57563804 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | (1S,2R)-1-[(2S,4R)-(4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-2-vinyl-cyclopropanecarboxylic acid ethyl ester | HCID 68409004 | — |
Reaction Steps
Compound 13 was kept in 30% trifluoroacetic acid in dichloromethane and 1% MeOH for 2 hrs before it was concentrated to dryness. The residue was re-dissolved in dichloromethane and during stirring 1N NaOH was added to pH 10-11. The organic layer was separated and concentrated which gave 1.6 g of the title product. HPLC purity ca. 90% M+H+ 269.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07700552B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-8f47213811e9414995c0684fa93e2e4f |
| Source note | uspto-grants-2010_04 |