関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Potassium Iodide | HCID 4875 | — |
| 反応物 | Sodium Chloride | HCID 5234 | — |
| 反応物 | Bromoacetic Acid | HCID 6227 | — |
| 反応物 | Potassium Hydroxide | HCID 14797 | — |
| 反応物 | tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate | HCID 11078078 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | tert-Butanol | HCID 6386 | — |
| 生成物 | HCID 54137898 | HCID 54137898 | 78.2% |
反応手順
A mixture of (2S,4R)-4-t-butyldimethylsilyloxy-1-t-butoxycarbonyl-2-(hydroxymethyl)pyrrolidine (0.62 g), 2-bromoacetic acid (0.26 g), 85% potassium hydroxide (0.37 g), and potassium iodide (0.93 g) in t-butyl alcohol (12 ml) was heated at 50° C. for 3 hours. The mixture was poured into water (100 ml), adjusted to pH 4 with 1N hydrochloric acid and saturated with sodium chloride. The aqueous mixture was extracted with three 50 ml portions of ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (30 g ) eluting with a mixture of methanol and dichloromethane (1:9 V/V) to give (2S,4R)-1-t-butoxycarbonyl-4-t-butyldimethylsilyloxy-2-(carboxymethyloxymethyl)pyrrolidine (0.57 g).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US04822787 |
|---|
| 出典データセット | uspto-grants-1989_04 |
|---|
| ORD ID | ord-cca902987ef84e6990b3784a70923176 |
|---|
| 出典メモ | uspto-grants-1989_04 |
|---|
