Acetic Anhydride → HCID 178476597, 화합물

HRID 245764노트

반응식

HRID 245764 반응식
[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]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 178523098HCID 178523098, 화합물

생성물 1

HCID 178476597HCID 178476597, 화합물수율 92.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-8341666057b442f7ad4556243044767d
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658794B2

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