Tetrahydrofuran → HCID 57526969, compound

HRID 1452589Notes

Reaction equation

HRID 1452589 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[C:21]([C:23]([O:25]CC)=[O:24])[CH:20]=[N:19]2)=[C:14]([F:28])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[OH-].[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[CH:20]=[N:19]2)=[C:14]([F:28])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 10833820HCID 10833820, compound

Product 1

HCID 57526969HCID 57526969, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Ethyl 1-(4-{[benzyloxycarbonyl]amino}-2-fluorophenyl)-1H-pyrazole-4-carboxylate (J. Med. Chem, 2000, 43, 5, p 953) (1.33 g, 3.45 mmol) was taken up in ethanol/water (1/1, 80 ml), tetrahydrofuran (10 ml) was added, followed by aqueous sodium hydroxide solution (1M, 155 ml) and it was stirred at room temperature for 5 hours. The organic solvents were removed and the aqueous solution was acidified with 1M aqueous hydrochloric acid. The acidic solution was extracted with ethyl acetate, dried over magnesium sulfate and the solvent removed under reduced pressure to give the title product (1.1 g).

Workup

  1. customThe organic solvents were removed
  2. extractionThe acidic solution was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b0892ca1791c486a84c850d335508f8d
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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