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Butyl nitrite → 3-(Dipropylcarbamoyl)benzoic acid
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Butyl nitrite | HCID 10996 | — |
| 反応物 | N-Boc-cis-4-hydroxy-D-proline | HCID 688616 | — |
| 反応物 | 3-Bromo-5-(methoxycarbonyl)benzoic acid | HCID 22593641 | — |
| 反応物 | (4R)-1-Boc-4-(2-propen-1-yloxy)-D-proline | HCID 67315699 | — |
| 触媒 | Copper bromide (CuBr2) | HCID 24611 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Acetonitrile | HCID 6342 | — |
| 生成物 | 3-(Dipropylcarbamoyl)benzoic acid | HCID 182769 | 97% |
反応手順
Step G (2): 3-bromo-5-(methoxycarbonyl)benzoic acid. To a mixture of copper (II) bromide (5.5 g, 24.6 mmol), n-butyl nitrite (3.17 g, 30.75 mmol) and acetonitrile (300 mL) was added 3-amino-5-(methoxycarbonyl)benzoic acid (Step G (1), 4.0 g, 20.5 mmol) in aceonitrile (300 mL) over 30 min at 0° C. and the mixture was warmed up and stirred at rt for 3 h. H2O was added and acetonitrile was removed. Ethyl acetate (600 mL) was added and the mixture was washed with 3N HCl, H2O, dried over Na2SO4, and concentrated in vacuo to give the title compound (97% yield): 1H NMR (CDCl3, 500 MHz) δ ppm 3.96 (3H, s), 8.41 (1H, s), 8.41 (1H, s), 8.67 (1H, m). MS (ESI) (M−H)− 259.02.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07745470B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-f1e12c8ab4c14f8c9ebf66d37ccca20b |
| 出典メモ | uspto-grants-2010_06 |