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Hydrochloric Acid → (R)-2-(1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | Sulfuryl chloride | HCID 24648 | — |
| 反応物 | Indole-5-carbonitrile | HCID 27513 | — |
| 反応物 | 2-Phenyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid | HCID 88327 | — |
| 反応物 | (R)-2-(1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid | HCID 53363877 | — |
| 触媒 | Tetrabutylammonium hydrogen sulfate | HCID 94433 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | (R)-2-(1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid | HCID 53363877 | — |
| 生成物 | (R)-2-(1-(Phenylsulfonyl)-1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid | HCID 53363878 | — |
反応手順
(R)-2-(1H-indol-5-yl)-4,5-dihydrothiazole-4-carboxylic acid 63a was synthesized using the same method as used for 42a from 1H-indole-5-carbonitrile and used without further purification. To a vigorously stirring solution of 63a (1 mmol) and tetrabutylammonium hydrogen sulfate (0.15 mmol) in toluene (10 mL) at 0° C. was added 50% aqueous sodium hydroxide (10 mL) and sulfonyl chloride (2 mmol). The resultant solution was stirred at RT for 6 h. Then 1 N HCl was added to acidify the mixture to pH=2 and extracted with CH2Cl2, the organic layer was separated and dried (MgSO4); then evaporated to dryness to yield 64a, which were used in subsequent steps without further purification.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08822513B2 |
| 出典データセット | uspto-grants-2014_09 |
| ORD ID | ord-9f1a7920997342cfa2aba54ae6ff5762 |
| 出典メモ | uspto-grants-2014_09 |