Acetic Anhydride → HCID 24894448、化合物

HRID 1913399ノート

反応式

HRID 1913399 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([NH2:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[C:11]([CH3:23])=[C:10]([C:24](=[O:27])[CH2:25][CH3:26])[CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C1COCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:35]([NH:22][S:19]([C:16]1[CH:15]=[CH:14][C:13]([N:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:9][C:10]([C:24](=[O:27])[CH2:25][CH3:26])=[C:11]2[CH3:23])=[CH:18][CH:17]=1)(=[O:20])=[O:21])(=[O:37])[CH3:36]

参加物

7

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 23642319A-867744

生成物 1

HCID 24894448HCID 24894448、化合物

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-[5-(4-chloro-phenyl)-2-methyl-3-propionyl-pyrrol-1-yl]-benzenesulfonamide (Example 31, 0.12 g, 0.31 mmol) in dry THF (5 mL) was added triethylamine (0.4 mmol, 0.06 mL) and DMAP (0.031 mmol, 4 mg) at room temperature. 10 Minutes later acetic anhydride (0.62 mmol, 0.06 mL) was added drop wise and the mixture stirred at room temperature for 16 hours. The mixture was diluted with ethyl acetate (100 mL), washed with sodium bicarbonate (saturated solution, 50 mL), water (50 mL) and brine (50 mL). The organic phase was dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified over silica using CH2Cl2:MeOH (95:5) as eluant to provide the titled compound. 1H NMR (CDCl3) δ ppm 1.18 (3H), 2.05 (3H), 2.16 (3H), 2.45 (2H), 3.39 (2H), 6.90 (1H), 7.33-7.90 (8H), 8.50 (1H); MS (ESI) m/z 445 (M+H).

後処理

  1. washwashed with sodium bicarbonate (saturated solution, 50 mL), water (50 mL) and brine (50 mL)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified over silica

出典と根拠

ORDレコード
ord-35b0a15f4b4b4cb4bdf10f5285003cb4
出典データセット
uspto-grants-2013_12
特許番号
US08609713B2

反応ノート

読み込み中…