Lithium hydroxide, monohydrate → HCID 11235124, compound

HRID 1176798Notes

Reaction equation

HRID 1176798 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1([NH:13][C:14]([C:16]2[O:17][C:18]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[CH:25][CH:24]=3)=[CH:19][CH:20]=2)=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7]>O.O1CCCC1.CO>[C:26]1([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:25]=[CH:24][C:23]([O:22][CH2:21][C:18]2[O:17][C:16]([C:14]([NH:13][C:8]3([C:6]([OH:7])=[O:5])[CH2:9][CH2:10][CH2:11][CH2:12]3)=[O:15])=[CH:20][CH:19]=2)=[CH:28][CH:27]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59694990HCID 59694990, compound

Product 1

HCID 11235124HCID 11235124, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (0.085 g, 2.0 mmol) in water (1 mL) was added to a solution of 1-{[5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-amino}-cyclopentanecarboxylic acid methyl ester (0.092 g, 0.22 mmol) in tetrahydrofuran (3 mL) and methanol (1 mL). The mixture was stirred overnight at room temperature and then the solvents were evaporated under reduced pressure. 0.5 M NaOH was added and the solution was extracted with ether. The aqueous layer was acidified with 1 M HCl and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried (sodium sulfate), filtered, and evaporated to give 1-{[5-(biphenyl-4-yloxymethyl)-furan-2-carbonyl]-amino}-cyclopentanecarboxylic acid (61 mg, 69%) as a white solid.

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. addition0.5 M NaOH was added
  3. extractionthe solution was extracted with ether
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. dry with materialThe combined organic layers were dried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-aa64220b7bf14c3995aa645ef486b608
Source dataset
uspto-grants-2010_11
Patent number
US07842825B2

Reaction notes

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