Acetic Anhydride → HCID 178476597、化合物

HRID 245764ノート

反応式

HRID 245764 の反応式
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:19]([O:18][C@H:15]1[CH2:16][CH2:17][C@@H:12]([C:10](=[O:11])[NH:9][CH2:8][C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:13][CH2:14]1)(=[O:21])[CH3:20]

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 178523098HCID 178523098、化合物

生成物 1

HCID 178476597HCID 178476597、化合物収率 92.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

To (cis)-N-((3-chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide (57.4 mmol, 15.47 g) and 4-dimethylaminopyridine (5.74 mmol, 0.701 g) in pyridine (125 ml) at 0° C. was added dropwise acetic anhydride (60.2 mmol, 5.69 ml) and the mixture was stirred at room temperature for one hour. Then the reaction was quenched with 4 N hydrochloric acid to a pH of four and extracted with ethyl acetate three times. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was taken up in toluene and concentrated in vacuo again. The residue was dissolved in dichloromethane (100 ml) and washed with 1 M hydrochloric acid (100 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give (cis)-4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl acetate (16.5 g)

後処理

  1. customThen the reaction was quenched with 4 N hydrochloric acid to a pH of four
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. concentrationconcentrated in vacuo again
  6. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  7. washwashed with 1 M hydrochloric acid (100 ml)
  8. washThe organic layer was washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8341666057b442f7ad4556243044767d
出典データセット
uspto-grants-2014_02
特許番号
US08658794B2

反応ノート

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