Imidazole → (R)-N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamide

HRID 1351924노트

반응식

HRID 1351924 반응식
[I:1][CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:6]=1)[OH:4].N1C=CN=C1.[CH2:29]([Si:31](Cl)([CH2:34][CH3:35])[CH2:32][CH3:33])[CH3:30]>CN(C)C1C=CN=CC=1.CN(C)C=O.CCOC(C)=O.CCCCCCC>[CH2:12]([O:11][C:8]1[CH:9]=[CH:10][C:5]([C@@H:3]([O:4][Si:31]([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:29][CH3:30])[CH2:2][I:1])=[CH:6][C:7]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

8

반응물 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 53853223(R)-2-Iodo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanol

생성물 1

HCID 54211801(R)-N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamide수율 79%

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매2회HCID 8900Heptane용매2회

실험 절차

To a solution of (R)-2-iodo-1-[4-(phenylmethoxy)-3-[(methyl-sulfonyl)amino]phenyl]ethanol (938 mg, 2.1 mmol), imidazole (393 mg, 5.77 mmol) and 4-dimethylaminopyridine (22.5 mg, 0.184 mmol) in dimethylformamide (10 mL) is added triethylsilyl chloride (0.38 mL, 2.2 mmol) with stirring. One hour thereafter, the reaction is complete, and the reaction solution is diluted with EtOAc (150 mL) and heptane (15 mL). The organic phase is washed with water, a saturated aqueous copper sulfate solution and a saturated brine, and dried over magnesium sulfate. The filtrate is concentrated under reduced pressure to give a solid, which is dissolved in ethyl acetate. The mixture is diluted with heptane, and the precipitated crystals are collected by filtration. The collected solid is washed with heptane and dried in vacuo to give the desired (R)—N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamide (926 mg, yield: 79%).

후처리

  1. customOne hour
  2. washThe organic phase is washed with water
  3. dry with materiala saturated aqueous copper sulfate solution and a saturated brine, and dried over magnesium sulfate
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customto give a solid, which
  6. filtrationthe precipitated crystals are collected by filtration
  7. washThe collected solid is washed with heptane
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-e84779e2b78848858f6d45b04eeb01fb
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217724B2

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