Lithium Hydroxide → 2-[(4-{2-[(Benzylsulfonyl)amino]ethyl}phenoxy)methyl]benzoic acid

HRID 2111987Notes

Reaction equation

HRID 2111987 reaction equation
[OH-].[Li+].[CH2:3]([S:10]([NH:13][CH2:14][CH2:15][C:16]1[CH:33]=[CH:32][C:19]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([O:26]C)=[O:25])=[CH:18][CH:17]=1)(=[O:12])=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.C1COCC1>[CH2:3]([S:10]([NH:13][CH2:14][CH2:15][C:16]1[CH:33]=[CH:32][C:19]([O:20][CH2:21][C:22]2[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=2[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=1)(=[O:11])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68869255Methyl 2-[(4-{2-[(benzylsulfonyl)amino]ethyl}phenoxy)methyl]benzoate

Product 1

HCID 100710622-[(4-{2-[(Benzylsulfonyl)amino]ethyl}phenoxy)methyl]benzoic acidYield 61.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (2 mg, 0.077 mmol) in water (0.5 ml) was added into methyl 2-[(4-{2-[(benzylsulfonyl)amino]ethyl}phenoxy)methyl]benzoate (17 mg, 0.038 mmol) dissolved in THF (1 ml). The mixture was then in irradiated in a microwave oven (Smith Synthesizer) at 150° C. for 7 minutes and then evaporated to remove THF. The residue was acidified with 1% hydrochloric acid, pH˜4, and extracted with ethyl acetate (×2). The organic extracts were combined and dried with MgSO4 and then evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 500 mg/3 ml) using DCM, then MeOH/DCM (0.5:99.5) as eluant gave 10 mg the desired product, yield 61%.

Workup

  1. customin irradiated in a microwave oven (Smith Synthesizer) at 150° C. for 7 minutes
  2. customevaporated
  3. customto remove THF
  4. extractionextracted with ethyl acetate (×2)
  5. dry with materialdried with MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-2b67e3e7ec134789bc41650e0955954f
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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