Lithium Hydroxide → HCID 57541089, compound

HRID 545374Notes

Reaction equation

HRID 545374 reaction equation
C[O:2][C:3](=[O:41])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:30]=3)[N:13]([CH3:28])[C:14]=2[C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:19][CH2:18]2)=[O:16])=[CH:6][CH:5]=1.[OH-].[Li+]>C1COCC1.CO>[CH2:35]([C:31]1[CH:30]=[C:29]([C:12]2[N:13]([CH3:28])[C:14]([C:15]([N:17]3[CH2:18][CH2:19][CH:20]([N:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[CH2:21][CH2:22]3)=[O:16])=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:41])=[O:2])=[CH:5][CH:6]=3)[N:11]=2)[CH:34]=[CH:33][CH:32]=1)[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57541080HCID 57541080, compound

Product 1

HCID 57541089HCID 57541089, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 0.15 g (0.27 mmol) of 4-[2-(3-hexyl-phenyl)-1-methyl-5-(4-pyrrolidin-1-yl-piperidine-1-carbonyl)-1H-imidazol-4-yl]-benzoic acid methyl ester (example 10) in 10 ml of THF/MeOH 1:1 was added drop by drop 0.67 ml (0.67 mmol) of lithium hydroxide solution (1 molar in water) and the reaction mixture was heated up to 50° C. After 10 hours, the solvents were evaporated and the residue poured into crashed ice, acidified with HCl (25% in water) and extracted twice with CH2Cl2/2-propanol 4:1; the organic phases were dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1) to give 0.13 g (89%) of the title compound as light brown solid. MS: 541.2 ([M-H]−).

Workup

  1. customthe solvents were evaporated
  2. additionthe residue poured
  3. extractionextracted twice with CH2Cl2/2-propanol 4:1
  4. dry with materialthe organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 9:1)

Sources & evidence

ORD record
ord-33d6328f3db949efbe8ff2c48aa18ee8
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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