HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → Z-Ser-NHNH-Boc
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | tert-Butyl carbazate | HCID 70091 | — |
| Reactant | 3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione | HCID 89529 | — |
| Reactant | N-(Benzyloxycarbonyl)-L-serine | HCID 100310 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Z-Ser-NHNH-Boc | HCID 13469056 | — |
Reaction Steps
Z-Ser-OH (10.0 g) and 6.2 g of t-butyl carbazate were dissolved in 150 ml of DMF and the solution was ice-cooled. HONB (8.0 g) and 9.3 g of DCC were added and the mixture was stirred for 15 hours. The formed DCU was filtered off and the filtrate was concentrated. The residue was extracted into AcOEt and the AcOEt solution was washed with 4% aqueous NaHCO3 and 10% aqueous citric acid, dried over Na2SO4 and concentrated. Ether was added and the crystals was collected by filtration. Yield 7.3 g (50.4%), mp 95°-98° C., [α]D26 -6.2° (c=0.8, DMF), Rf1 0.62.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04681848 |
| Source dataset | uspto-grants-1987_07 |
| ORD ID | ord-80daa5f88ed14b4a94aff7fb10fdef83 |
| Source note | uspto-grants-1987_07 |