HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → HCID 131712284, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione | HCID 89529 | — |
| Reactant | Glycine tert-butyl ester | HCID 151417 | — |
| Reactant | Z-D-Thr-OH | HCID 853484 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 131712284 | HCID 131712284 | 69.1% |
Reaction Steps
In 50 ml of THF are dissolved 5.0 g of Z-(D)-Thr-OH and 3.6 g of H-Gly-OBut. After cooling, 3.9 g of HONB and 4.5 g of DCC are added, and the mixture is stirred overnight. The solvent is distilled off, and the residue is extracted with 100 ml of AcOEt, followed by washing with water and drying over anhydrous sodium sulphate. The AcOEt is distilled off, and the residue is treated with petroleum ether. Recrystallization from AcOEt-petroleum ether yields 5.0 g of the desired compound. m.p. 56°-57° C., [α]D23 +13.8° (c=0.5, MeOH), Rf1 =0.69.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04277394 |
| Source dataset | uspto-grants-1981_07 |
| ORD ID | ord-fa8911d41a0d4cfe9c9b18dd77cd9ea5 |
| Source note | uspto-grants-1981_07 |