HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → 5-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid 1-tert-butyl ester 3-(2,5-dioxo-pyrrolidin-1-yl) ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate | HCID 9857522 | — |
| Reactant | 5-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid mono-tert-butyl ester | HCID 66724500 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid 1-tert-butyl ester 3-(2,5-dioxo-pyrrolidin-1-yl) ester | HCID 87125634 | — |
Reaction Steps
5-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid mono-tert-butyl ester (140 mg, 0.25 mmol) was dissolved in dry THF (3.5 ml). TSTU (95 mg, 0.30 mmol) and DIPEA (70 ul, 0.30 mmol) were added. The mixture was stirred at RT under nitrogen over the week-end. The reaction mixture was almost dry. EtOAc was added and the precipitate was removed by filtration. The filtrate was extracted with 0.1 N HCl (2×), brine (1×), dried (Na2SO4) and concentrated to give the title compound as a syrup containing a trace of an impurity in a quantitative yield (0.165 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08476228B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-3952a3c47a4d442bba89141f86fddeb0 |
| Source note | uspto-grants-2013_07 |