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(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile → (3R,4S)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | (3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile | HCID 10943936 | — |
| 反応物 | (2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid | HCID 22860073 | — |
| 溶媒 | Ethanol | HCID 702 | — |
| 生成物 | (3R,4S)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile | HCID 14511095 | 58.7% |
| 生成物 | (2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid | HCID 22860073 | — |
反応手順
A mixture of trans-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (32.74 g) and (+)-di-p-toluoyl-D-tartaric acid (57.95 g) was dissolved in ethanol (85 ml) under reflux. The mixture was cooled to room temperature and stood for 4 days to give a white precipitate. This precipitate was collected by filtration, washed with a mixture of ethanol and diisopropyl ether (100 ml, 1:2), and recrystallized from ethanol (80 ml) to give (+)-di-p-toluoyl-D-tartaric acid salt of (3R,4S)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (19.20 g).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US04988723 |
| 出典データセット | uspto-grants-1991_01 |
| ORD ID | ord-81d6b01d2c2a468ca4c5f8cdc5e0bd14 |
| 出典メモ | uspto-grants-1991_01 |