関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | Benzyloxycarbonylglycine | HCID 14349 | — |
| 反応物 | 2-Bromo-1,1-dimethoxyethane | HCID 81672 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 2,2-dimethoxyethyl N-benzyloxycarbonylglycine | HCID 67185485 | 61.2% |
反応手順
A mixture of N-α-CBZ-glycine (2.0 g, 9.57 mmol), bromoacetaldehyde dimethyl acetal (2.25 mL, 19.13 mmol) and Cs2CO3 (2.78 g, 3.12 mmol) in 20 mL of anhydrous DMF was stirred at 100° C. for 24 h. After cooling to room temperature, water was added and the mixture was extracted with ethyl acetate (3×80 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using 45-50% ethyl acetate/hexanes to give the product 37 (1.74 g, 61%). 1H NMR (400 MHz, CDCl3) δ 3.38 (s, 6H), 3.98 (d, J=5.7 Hz, 2H), 4.12 (d, J=5.3 Hz, 2H), 4.54 (t, J=5.3 Hz, 1H), 5.10 (s, 2H), 5.50 (bs, 1H), 7.32 (m, 5H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08524691B2 |
|---|
| 出典データセット | uspto-grants-2013_09 |
|---|
| ORD ID | ord-c1c0015e7ace4502a20afd5e8a5bf10e |
|---|
| 出典メモ | uspto-grants-2013_09 |
|---|
