反応式
Br[CH2:2][C:3]([N:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[C:10]#[N:11])=[O:4].[NH2:12][CH:13]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[C:21]([NH2:23])=[O:22])=[O:15]>C1COCC1>[C:10]([C@@H:6]1[CH2:7][CH2:8][CH2:9][N:5]1[C:3](=[O:4])[CH2:2][NH:12][C@@H:13]([CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]([N:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[C:21]([NH2:23])=[O:22])=[O:15])#[N:11]参加物
反応物 2
生成物 1
試薬・触媒・溶媒 1
実験手順
A solution of 1-(2-bromo-acetyl)-(S)-pyrrolidine-2-carbonitrile (44 mg, 0.2 mmol) in THF (1 mL) was added slowly to a cold solution (−15° C.) of 1-(2-amino-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid amide (55 mg, 0.24 mmol) in THF (2 mL). The temperature of the reaction mixture was gradually increased to room temperature. After stirring at this temperature overnight, the residue was concentrated and purified by LCMS to yield 1{(S)-2-[2-(2-Cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-(S)-4-methyl-pentanoyl}-(S)-pyrrolidine-2-carboxylic acid amide (54 mg; 62%). This pure product (20 mg) was dissolved in THF (1 mL), HCl ether (0.1 mL; 2M) was added and the mixture was concentrated to give the HCl salt form of 1-{(S)-2-[2-(2-cyano-pyrrolidin-1-yl)-2-oxo-ethylamino]-(S)-4-methyl-pentanoyl}-(S)-pyrrolidine-2-carboxylic acid amide. 1H-NMR data (CDCl3—CD3OD, 20:1): δ, 8.25 and 6.25 (s, 1H each), 4.73 (m, 1H), 4.43 (t, 1H, J=5.4 Hz), 4.2 (d, 1H, J=14.1 Hz), 4.0-3.47 (m, 7H), 2.4-1.9 (m, 10H), 1.41 (m, 1H). MS: calculated for C18H29N5O3+H 364.2; found: 364.2.
後処理
- concentrationthe residue was concentrated
- custompurified by LCMS
出典と根拠
- ORDレコード
- ord-bfd648cc78ae46c68e288b9739fdfe8b
- 出典データセット
- uspto-grants-2009_12
- 特許番号
- US07638638B2
関連ノート
読み込み中…