Water → 7-(4-((2-phenylcyclopropyl)carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylic acid

HRID 1021430Notes

Reaction equation

HRID 1021430 reaction equation
[C:1]1([CH:7]2[CH2:9][CH:8]2[NH:10][C:11]([C:13]2[CH:35]=[CH:34][C:16]([O:17][C:18]3[CH:27]=[C:26]4[C:21]([CH:22]([C:28]([O:30]C)=[O:29])[CH2:23][CH2:24][O:25]4)=[CH:20][C:19]=3[C:32]#[N:33])=[CH:15][CH:14]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>C1COCC1.FC(F)(F)C(O)=O>[C:1]1([CH:7]2[CH2:9][CH:8]2[NH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:17][C:18]3[CH:27]=[C:26]4[C:21]([CH:22]([C:28]([OH:30])=[O:29])[CH2:23][CH2:24][O:25]4)=[CH:20][C:19]=3[C:32]#[N:33])=[CH:34][CH:35]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 962WaterHCID 67080429methyl 7-(4-((2-phenylcyclopropyl)carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate

Product 1

HCID 670801677-(4-((2-phenylcyclopropyl)carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylic acidYield 30.6%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 7-(4-((2-phenylcyclopropyl)carbamoyl)phenoxy)-6-cyano-3,4-dihydro-2H-chromene-4-carboxylate (25.9 mg, 0.0553 mmol) was dissolved in THF (1.5 ml) and 1M LiOH-monohydrate solution in water (0.111 ml, 0.111 mmol) was added. The mixture was stirred for 17 hours at ambient temperature. A few drops of trifluoroacetic acid were added to the mixture and the mixture was purified on silica gel (MeOH in dichloromethane gradient with 1% acetic acid) to provide 7.7 mg of the title compound as a thin film (30%). MS (apci) m/z=453.0 (M−H).

Workup

  1. customthe mixture was purified on silica gel (MeOH in dichloromethane gradient with 1% acetic acid)

Sources & evidence

ORD record
ord-ac49fcdfe2014898b829ce6aba6ee6b3
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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