関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | p-Toluenesulfonic acid | HCID 6101 | — |
| 反応物 | Dicyclohexylcarbodiimide | HCID 10868 | — |
| 反応物 | L-Glutamine, N2-[(phenylmethoxy)carbonyl]- | HCID 75855 | — |
| 反応物 | 3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione | HCID 89529 | — |
| 反応物 | L-Tryptophan benzyl ester | HCID 7016092 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | Z-Gln-Trp-OBzl | HCID 131712662 | — |
反応手順
In 500 ml of THF is dissolved 50.0 g of H-Trp-OBzl. p-toluenesulfonate, and under ice-cooling, 15.4 ml of TEA, 28.0 g of Z-Gln-OH, 19.7 g of HONB and 22.7 g of DCC are added. The mixture is stirred for 15 hours. The precipitated DCU is filtered off, the filtrate concentrated and the residue dissolved in 300 ml of ethyl acetate. The solution is washed with saturated aqueous sodium hydrogen carbonate (150 ml×2), 10% aqueous citric acid (150 ml×2) and water (150 ml×2) in the order mentioned. The solvent is distilled off under reduced pressure, the residue dissolved in 300 ml of THF and the insolubles are filtered off. The filtrate is concentrated and precipitated with 500 ml of diethyl ether. The resultant powders are collected by filtration and recrystallized from acetonitrile. Yield 46.1 g (82.8%); [α]D23 +5.8°(c=1.0, DMF); Rf1 =0.60.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US04312943 |
|---|
| 出典データセット | uspto-grants-1982_01 |
|---|
| ORD ID | ord-e7d34bca021c4b7791bce6297ca14fc3 |
|---|
| 出典メモ | uspto-grants-1982_01 |
|---|
