참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | p-Toluenesulfonic acid | HCID 6101 | — |
| 반응물 | Dicyclohexylcarbodiimide | HCID 10868 | — |
| 반응물 | L-Glutamine, N2-[(phenylmethoxy)carbonyl]- | HCID 75855 | — |
| 반응물 | 3a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione | HCID 89529 | — |
| 반응물 | L-Tryptophan benzyl ester | HCID 7016092 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | Z-Gln-Trp-OBzl | HCID 131712662 | — |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US04312943 |
|---|
| 출처 데이터셋 | uspto-grants-1982_01 |
|---|
| ORD ID | ord-e7d34bca021c4b7791bce6297ca14fc3 |
|---|
| 출처 메모 | uspto-grants-1982_01 |
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