Lithium hydroxide, monohydrate → 4-(4-(2-Tert-butoxy-2-oxoethyl)-2-(methylsulfonamido-methyl)phenoxy)benzoic acid

HRID 453493Notes

Reaction equation

HRID 453493 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]C)=[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].O[Li].O>O1CCOCC1.O.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:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[C:10]([CH2:25][NH:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:9]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68468952Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamidomethyl)phenoxy)benzoate

Product 1

HCID 684645984-(4-(2-Tert-butoxy-2-oxoethyl)-2-(methylsulfonamido-methyl)phenoxy)benzoic acidYield 81.5%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

The product of step C (900 mg, 2.00 mmol) was diluted with dioxane (10 mL) followed by the addition of LiOH—H2O (126 mg, 3.00 mmol) dissolved in water (2 mL). After stirring for 12 hours, the reaction mixture was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a biotage 40M cartridge eluting with methylene chloride:MeOH (95:5) to yield 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamido-methyl)phenoxy)benzoic acid (710 mg, 81.4% yield) as a clear oil.

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was purified
  6. washeluting with methylene chloride:MeOH (95:5)

Sources & evidence

ORD record
ord-8689a0edd1d3482fb11a0144e5b99917
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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