참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Hydrochloric Acid | HCID 313 | — |
| 반응물 | Potassium Iodide | HCID 4875 | — |
| 반응물 | Sodium Chloride | HCID 5234 | — |
| 반응물 | Bromoacetic Acid | HCID 6227 | — |
| 반응물 | Potassium Hydroxide | HCID 14797 | — |
| 반응물 | tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate | HCID 11078078 | — |
| 용매 | Water | HCID 962 | — |
| 용매 | tert-Butanol | HCID 6386 | — |
| 생성물 | HCID 54137898 | HCID 54137898 | 78.2% |
반응 단계
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).
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US04822787 |
|---|
| 출처 데이터셋 | uspto-grants-1989_04 |
|---|
| ORD ID | ord-cca902987ef84e6990b3784a70923176 |
|---|
| 출처 메모 | uspto-grants-1989_04 |
|---|
