Tetrahydrofuran → HCID 58963169, compound

HRID 917529Notes

Reaction equation

HRID 917529 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:15]2[CH:16]=[C:17]([CH2:25][CH3:26])[C:18]3[O:22][CH:21]=[C:20]([CH3:23])[C:19]=3[CH:24]=2)[C:11]([O:13]C)=[O:12])=[CH:5][CH:4]=1)#[N:2].O[Li].O.C1COCC1>O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH:10]([C:15]2[CH:16]=[C:17]([CH2:25][CH3:26])[C:18]3[O:22][CH:21]=[C:20]([CH3:23])[C:19]=3[CH:24]=2)[C:11]([OH:13])=[O:12])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 58963165HCID 58963165, compound

Product 1

HCID 58963169HCID 58963169, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 2-(4-cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetate 5 (1.11 g, 3.18 mmol), LiOH.H2O (700 mg, 15.9 mmol), THF (10 mL) and water (5 ml) was stirred vigorously for 3 h. The mixture was partitioned between 1N HCl (100 ml) and ethyl acetate (100 ml). The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine (1×125 mL), dried (MgSO4), filtered, and concentrated to yield 1.09 g (98%) of 2-(4-cyanophenylamino)-2-(7-ethyl-3-methylbenzofuran-5-yl)acetic acid 6 as an off-white solid.

Workup

  1. customThe mixture was partitioned between 1N HCl (100 ml) and ethyl acetate (100 ml)
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layers were washed with brine (1×125 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3f040840d976432d921392fa1c3c3d2b
Source dataset
uspto-grants-2007_09
Patent number
US07273886B2

Reaction notes

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