関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 反応物 | Trifluoromethanesulfonic anhydride | HCID 67749 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 2-(Tricyclo(3.3.1.1'3,7)dec-1-yl)ethanol | HCID 110810 | — |
| 反応物 | N(alpha), N-(im)-Di-Boc-L-histidine methyl ester | HCID 10904703 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | HCID 18631278 | HCID 18631278 | — |
反応手順
A solution of 11.8 mL trifluoromethanesulfonic anhydride in 70 mL dichloromethane is chilled to -70° C. and treated dropwise with a solution composed of 12.6 g 1-adamantyl-2-hydroxyethane, 12.2 mL diisopropylethylamine and 70 mL dichloromethane. The solution is allowed to warm to -55° C. over 45 min then a solution of 25 g N,1-bis-BOC-histidine methyl ester (J. Chem. Soc., Perkin Trans. I 1982; 1553-61.) in 70 mL dichloromethane is added dropwise. The reaction is then stirred at 25° C. for 24 hr and poured into pH=7, 0.25M potassium phosphate buffer (500 mL), stirring vigorously. The organic layer is separated, washed with the same buffer, dried and concentrated. 3-(2-(1-Adamantyl)ethyl)-N-BOC-histidine methyl ester is isolated by chromatography on silica gel (chloroform-methanol, 99:1) as a gum. NMR (CDCl3) 3.85 (m, 2H, NCH2).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US04816463 |
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| 出典データセット | uspto-grants-1989_03 |
|---|
| ORD ID | ord-c882b85770e9485eb1def7c4898e5720 |
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| 出典メモ | uspto-grants-1989_03 |
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