HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzyl chloroformate → HCID 66847059, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzyl chloroformate | HCID 10387 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Dichloromethane ethylacetate | HCID 21226138 | — |
| Reactant | (8S,11S,14S)-14-Amino-11-isobutyl-10,13-dioxo-2-oxa-9,12-diaza-bicyclo[14.2.2]icosa-1(19),16(20),17-triene-8-carboxylic acid methyl ester hydrochloride | HCID 66847433 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66847059 | HCID 66847059 | — |
Reaction Steps
Amine 25 (0.550 g, 1.17 mmol) was dissolved in anhydrous DMF (20 mL). Benzyl chloroformate (0.250 mL, 1.76 mmol) and DIPEA (0.815 mL, 4.68 mmol) were added and the reaction mixture was stirred at rt for 18 h before being partitioned between EtOAc and 1M hydrochloric acid. The aqueous phase was extracted twice more with EtOAc and the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc/DCM to yield an off-white solid, 0.460 g, 69%. Rf=0.32 (30% EtOAc/DCM). m.p. 91-93° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08710178B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-f225d6a3473748c782aedca48d3b769e |
| Source note | uspto-grants-2014_04 |