Lithium Hydroxide → 2-[(4-{2-[(2-Methyl-5-phenyl-3-furoyl)amino]ethyl}phenoxy)methyl]benzoic acid

HRID 2111985Notes

Reaction equation

HRID 2111985 reaction equation
[OH-].[Li+].[CH3:3][C:4]1[O:5][C:6]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:7][C:8]=1[C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:31]=[CH:30][C:17]([O:18][CH2:19][C:20]2[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=2[C:22]([O:24]C)=[O:23])=[CH:16][CH:15]=1)=[O:10]>O.C1COCC1>[CH3:3][C:4]1[O:5][C:6]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:7][C:8]=1[C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:31]=[CH:30][C:17]([O:18][CH2:19][C:20]2[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=2[C:22]([OH:24])=[O:23])=[CH:16][CH:15]=1)=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68869789Methyl 2-[(4-{2-[(2-methyl-5-phenyl-3-furoyl)amino]ethyl)phenoxy)methyl]benzoate

Product 1

HCID 100270332-[(4-{2-[(2-Methyl-5-phenyl-3-furoyl)amino]ethyl}phenoxy)methyl]benzoic acidYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (3.3 mg, 0.136 mmol) in water (1 ml) was added into methyl 2-[(4-{2-[(2-methyl-5-phenyl-3-furoyl)amino]ethyl}phenoxy)methyl]benzoate (32 mg, 0.068 mmol) dissolved in THF(2 ml). The mixture was then 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 washed with brine and dried with magnesium sulphate and then evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 2 g/6 ml) using DCM, then MeOH/DCM (1:99 and 2:98) as eluant gave 22 mg the desired product, yield 71%.

Workup

  1. customThe mixture was then 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. washwashed with brine
  6. dry with materialdried with magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-af1eb84f63f24a0284a9e858cfb5bc92
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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