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

HRID 1351924Notes

Reaction equation

HRID 1351924 reaction equation
[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

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×HCID 8900HeptaneSolvent2×

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-e84779e2b78848858f6d45b04eeb01fb
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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