methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2((N-methylmethylsulfonamido)methyl)phenoxy)benzoate → 4-(4(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoic acid

HRID 453545Notes

Reaction equation

HRID 453545 reaction equation
[C:1]([O:5][C:6](=[O:32])[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]C)=[O:18])=[CH:15][CH:14]=2)=[C:10]([CH2:25][N:26]([CH3:31])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.O.ClCCl.Cl>[C:1]([O:5][C:6](=[O:32])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[C:10]([CH2:25][N:26]([CH3:31])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:9]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 1

HCID 69322462methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2((N-methylmethylsulfonamido)methyl)phenoxy)benzoate

Product 1

HCID 693244814-(4(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoic acidYield 70.6%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoate (370 mg, 0.797 mmol) in dioxane (8 ml) was added a solution of LiOH monohydrate (43.5 mg, 1.04 mmol) in water (2 ml) (0.1M solution 4:1 dioxane/water). The reaction was stirred for 5 hours, then diluted with dichloromethane and 2N HCl. The aqueous phase was extracted with dichloromethane and the combined organic layers were washed with brine and dried over MgSO4. The crude product was purified by silica gel chromatography to give 4-(4-(2-tert-butoxy-2-oxoethyl)-2-((N-methylmethylsulfonamido)methyl)phenoxy)benzoic acid (0.253 g).

Workup

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

Sources & evidence

ORD record
ord-15021b84320a4de1a5345907efe04770
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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