Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydroxypyridinone | HCID 69975 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Glycine tert-butyl ester | HCID 151417 | — |
| Reactant | O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733286 | — |
| Reactant | (2R,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid | HCID 7408199 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | Fmoc-D-Hyp-Gly-OtBu | HCID 131717656 | — |
Reaction Steps
1.4 g of Fmoc-D-Hyp-OH are dissolved in 25 ml of dry acetonitrile and then 1.05 g of H-Gly-OtBu and 0.445 g of N-hydroxypyridone are added. Then 1.31 g of O-[(cyano(ethoxycarbonyl)methylidene)amino]-1,1,3,3-tetramethyluronium tetrafluoroborate (TOTU) are introduced in/portions within 10 minutes, as well as 1.03 ml of diisopropylethylamine in 15 ml of DMF dropwise over the course of 15 minutes. After 1 h, the mixture is concentrated, the residue is taken up in ethyl acetate and extraction with sodium chloride solution is carried out. The organic phase is dried over sodium sulfate and evaporated to dryness. The remaining oil is taken up in a little ether and added dropwise to petroleum ether while stirring. The flocculent precipitate is filtered off with suction and dried in vacuo.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05166394 |
|---|
| Source dataset | uspto-grants-1992_11 |
|---|
| ORD ID | ord-1c72ccf168904bfabd7b4c73a04aa3e8 |
|---|
| Source note | uspto-grants-1992_11 |
|---|
