Octanoyl chloride → HCID 71549357、化合物

HRID 1852359ノート

反応式

HRID 1852359 の反応式
[NH2:1][C@H:2]([CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C@@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[OH:4].CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>C1COCC1.CCOC(C)=O>[OH:4][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])[C@H:2]([NH:1][C:28](=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1

参加物

6

反応物 3

HCID 8124Octanoyl chlorideHCID 81531DiisopropylethylamineHCID 86680953HCID 86680953、化合物2 回

生成物 1

HCID 71549357HCID 71549357、化合物収率 22.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a 0° C. solution of (1R,2R)-2-amino-1-(2-methoxyphenyl)-3-(pyrrolidin-1-yl)propan-1-ol (0.1 g, 0.40 mmol) (compound 6) in THF (5 ml) was added Hunig's Base (0.07 g, 0.52 mmol), followed by the dropwise addition of octanoyl chloride (0.07 g, 0.40 mmol). The resulting mixture was allowed to stir overnight at room temperature, diluted with EtOAc, and washed with satd. aq. NaHCO3, satd. aq. NaCl, and dried over MgSO4. Purified by flash silica chromatography (MeOH/CH2Cl2) to give a yellow oil (0.03 g, 0.09 mmol, 22% yield). HPLC purity 93% (tR=5.3 min) NMR (500 MHz, CDCl3) δ 7.4 (m, 1H), 7.2-7.3 (m, 1H), 6.9-7.0 (m, 1H), 6.8-6.9 (m, 1H), 6.0-6.1 (m, 1H), 5.3 (d, 1H), 4.2-4.3 (m, 1H), 3.8 (s, 3H), 2.9-3.0 (m, 3H), 2.5-2.7 (m, 4H), 2.0-2.1 (m, 2H), 1.7-1.8 (m, 4H), 1.9-2.0 (m, 2H), 1.2-1.4 (m, 6H), 0.8-0.9 (t, 3H). ESI-MS m/z 377.2 (M+H +).

後処理

  1. washwashed with satd
  2. dry with materialaq. NaCl, and dried over MgSO4
  3. customPurified by flash silica chromatography (MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-c6d1b963e306440e9f2c84bd315e06e8
出典データセット
uspto-grants-2015_02
特許番号
US08961959B2

反応ノート

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