Methyl iodide → methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2((N-methylmethylsulfonamido)methyl)phenoxy)benzoate

HRID 1927776Notes

Reaction equation

HRID 1927776 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[C:10]([CH2:25][NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].CI.[C:34]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.Cl>[C:1]([O:5][C:6](=[O:31])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)=[C:10]([CH2:25][N:26]([CH3:34])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68468952Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamidomethyl)phenoxy)benzoate

Product 1

HCID 69322462methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2((N-methylmethylsulfonamido)methyl)phenoxy)benzoateYield 48.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamidomethyl)phenoxy)benzoate (745 mg, 1.65 mmol) in DMF (10 ml) was added MeI (155 μL, 2.48 mmol) followed by K2CO3 (343 mg, 2.48 mmol). The reaction was stirred at ambient temperature for 3 hours, then diluted with ethyl acetate and 2M HCl. The aqueous phase was extracted with ethyl acetate, and the combined organic layers were washed with brine and dried over MgSO4. The crude mixture was purified by silica gel chromatography to give methyl 4-(4-(2-tert -butoxy-2-oxoethyl)-2((N-methylmethylsulfonamido)methyl)phenoxy)benzoate (0.368 g).

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4744abeef2c14a02b32ec492d89da0dc
Source dataset
uspto-grants-2012_05
Patent number
US08183289B2

Reaction notes

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