Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | (7S,10S,13S)-10-Isopropyl-9,12-dioxo-13-[(1H-pyrrole-2-carbonyl)-amino]-2-oxa-8,11-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-7-carboxylic acid methyl ester | HCID 66846964 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86650245 | HCID 86650245 | — |
Reaction Steps
Ester 51 (45 mg) was dissolved in DCM (6 mL) under an atmosphere of argon. The reaction was cooled to −78° C. To the resultant solution DIBAL (0.5 mL) was added dropwise. This was stirred for 2 h before being allowed to warm to rt overnight. The reaction mixture was partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted again with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 1/1 EtOAc/(50/70) petroleum ether to EtOAc to yield a light brown solid, 14 mg, 33%. Rf=0.25 (1/1 EtOAc/(50/70) petroleum ether).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08710178B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-ab217bbab05b4c32a1382387a05c8810 |
|---|
| Source note | uspto-grants-2014_04 |
|---|
