Potassium Carbonate → (S)-N-(a-ethylbenzyl)-3-(cyanomethoxy)-2-phenylquinoline-4-carboxamide

HRID 651069

反応式

HRID 651069 の反応式
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[OH:29])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:37][C:38]#[N:39]>C1COCC1>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][CH2:37][C:38]#[N:39])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 5311424Talnetant

生成物 1

HCID 54316707(S)-N-(a-ethylbenzyl)-3-(cyanomethoxy)-2-phenylquinoline-4-carboxamide収率 95.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2.0 g (5.23 mmol) of (S)-N-(α-ethylbenzyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (compound of Description 1), 2.21 g of K2CO3, 0.26 g (1.57 mmol) of KI and 0.52 ml (7.85 mmol) of bromoacetonitrile were stirred in 30 ml of dry THF for 5 hours. The inorganic salts were filtered off and the filtrate was evaporated in vacuo to dryness. The residue was dissolved in CH2Cl2 and the organic phase was washed with H2O, sat. sol. NaHCO3, sat. sol. NaCl, separated, dried over Na2SO4 and evaporated in vacuo to dryness to afford 2.10 g of a brown oil which was flash chromatographed on 230-400 mesh silica gel, eluting with a mixture of hexane/EtOAc 70:30. The crude product was triturated with hexane, filtered, washed and dried to yield 0.75 g of the title compound as a white solid.

後処理

  1. filtrationThe inorganic salts were filtered off
  2. customthe filtrate was evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washthe organic phase was washed with H2O, sat. sol. NaHCO3, sat. sol. NaCl
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo to dryness

出典と根拠

ORDレコード
ord-95dae2f82a1d413f88ba57f8d055dba3
出典データセット
uspto-grants-2001_08
特許番号
US06277862B1

関連ノート

読み込み中…