Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1-Boc-D-Pyroglutamic acid ethyl ester | HCID 820885 | — |
| Reactant | HCID 178505773 | HCID 178505773 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67464674 | HCID 67464674 | — |
Reaction Steps
To a solution of (R)-5-oxopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (4.0 g) in tetrahydrofuran (100 mL), 3-fluorophenylmagnesium bromide (1.0 M solution in tetrahydrofuran; 17.1 mL) was added dropwise at −40° C. over 10 minutes, and the reaction solution was stirred at −40° C. to 0° C. for one hour. Water was added to the solution in small portions at 0° C., followed by extraction from the reaction solution with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to obtain 5.5 g of the title compound as a colorless oil. The property values of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08048878B2 |
|---|
| Source dataset | uspto-grants-2011_11 |
|---|
| ORD ID | ord-75734ac16ba34cc0b2e96aadc30d758c |
|---|
| Source note | uspto-grants-2011_11 |
|---|