Dichloromethane → Methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester

HRID 1421779노트

반응식

HRID 1421779 반응식
[OH:1][CH2:2][CH2:3][CH:4]([C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.C(Cl)Cl.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(C(C)C)CC)(C)C>C1COCC1>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([CH:4]([N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)[CH2:3][CH2:2][O:1][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:11][CH:12]=1)#[N:15]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 187796904-(3-Hydroxy-1-imidazol-1-yl-propyl)-benzonitrile

생성물 1

HCID 54062353Methanesulfonic acid 3-(4-cyano-phenyl)-3-imidazol-1-yl-propyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The 4-(3-hydroxy-1-imidazol-1-yl-propyl)-benzonitrile (1.4 gm, 6.16 mmol) was suspended in 2:1 methylene chloride: THF (100 mL) under argon and cooled to 0° C. in an ice bath. Methanesulfonylchloride (1 mL, 12.4 mmol) was added followed by diisopropylethylamine (3.22 mL, 18.5 mmol). The reaction was stirred for 4 hours and the solvent was removed in vacuo. The residue was suspended in ethyl acetate (200 mL) and extracted 2 times with saturated aqueous sodium bicarbonate (100 mL), then water (100 mL), then saturated sodium chloride solution (100 mL). The organic solvent was removed in vacuo and the residue was chromatographed on silica gel using using 1:3 ethyl acatate: hexanes. The desired fractions were concentrated in vacuo to give the desired product.

후처리

  1. customthe solvent was removed in vacuo
  2. extractionextracted 2 times with saturated aqueous sodium bicarbonate (100 mL)
  3. customThe organic solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel using
  5. concentrationThe desired fractions were concentrated in vacuo

출처 및 근거

ORD 기록
ord-ece0b03db92c4970b0ad401c2cb5bdfd
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077853

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