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

HRID 1351924ノート

反応式

HRID 1351924 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒2 回HCID 8900Heptane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e84779e2b78848858f6d45b04eeb01fb
出典データセット
uspto-grants-2007_05
特許番号
US07217724B2

反応ノート

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