Lithium Hydroxide → HCID 10367746, compound

HRID 2111979Notes

Reaction equation

HRID 2111979 reaction equation
[OH-].[Li+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][N:15]([CH3:38])[C:16](=[O:37])[CH2:17][CH2:18][C:19]2[CH:36]=[CH:35][C:22]([O:23][CH2:24][C:25]3[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=3[C:27]([O:29]C)=[O:28])=[CH:21][CH:20]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]>O.C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][CH2:14][N:15]([CH3:38])[C:16](=[O:37])[CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25]3[CH:34]=[CH:33][CH:32]=[CH:31][C:26]=3[C:27]([OH:29])=[O:28])=[CH:35][CH:36]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68868645HCID 68868645, compound

Product 1

HCID 10367746HCID 10367746, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (12 mg, 0.488 mmol) in water (1 ml) was added to methyl 2-[(4-{3-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]-3-oxopropyl}phenoxy)methyl]benzoate (120 mg, 0.244 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) as eluant gave 102 mg the desired product, yield 87.5%.

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-d8d10bafcd5b4b2b84319c55bfe8f634
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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