Tetrahydrofuran → HCID 178504281、化合物

HRID 470700ノート

反応式

HRID 470700 の反応式
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].O1CCCC1.[NH2:18]/[C:19](=[N:36]\[OH:37])/[C@H:20]1[CH2:25][CH2:24][C@H:23]([NH:26][C:27](=[O:35])[O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH2:22][CH2:21]1>ClCCl>[O:2]=[C:1]1[O:37][N:36]=[C:19]([C@H:20]2[CH2:21][CH2:22][C@H:23]([NH:26][C:27](=[O:35])[O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:32])[CH3:34])[CH2:24][CH2:25]2)[NH:18]1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 178504282HCID 178504282、化合物

生成物 1

HCID 178504281HCID 178504281、化合物収率 62.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

Carbonyldiimidazole (1.24 g, 7.43 mmol) was added to a tetrahydrofuran (20 ml) solution of the compound (1.12 g, 3.71 mmol) obtained in Step 5 above under ice cooling and the resulting mixture was stirred at 50° C. for 24 hours. The reaction mixture was diluted with dichloromethane:methanol [10:1 (v/v)] and washed with 10% aqueous citric acid solution and saturated sodium bicarbonate solution in that order and then the organic layer was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1→13:7→dichloromethane:methanol=49:1→19:1 (v/v)] to give 757 mg (62%) of the title compound as a colorless solid.

後処理

  1. washmethanol [10:1 (v/v)] and washed with 10% aqueous citric acid solution and saturated sodium bicarbonate solution in that order
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customthe residue obtained
  5. customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=9:1→13:7→dichloromethane:methanol=49:1→19:1 (v/v)]

出典と根拠

ORDレコード
ord-34b4ef73b0774e7fb6ac1d905a658440
出典データセット
uspto-grants-2014_01
特許番号
US08629133B2

反応ノート

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