Lithium hydroxide, monohydrate → HCID 67287160, compound

HRID 1626403Notes

Reaction equation

HRID 1626403 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:32])[NH:21][C:22]3[CH:23]=[N:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=3)=[CH:16][C:15]=1[CH3:33])[O:9][CH2:8][CH2:7][CH:6]2[C:34]([O:36]C)=[O:35])#[N:2].O[Li].O>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:32])[NH:21][C:22]3[CH:23]=[N:24][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:27]=3)=[CH:16][C:15]=1[CH3:33])[O:9][CH2:8][CH2:7][CH:6]2[C:34]([OH:36])=[O:35])#[N:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67289903HCID 67289903, compound

Product 1

HCID 67287160HCID 67287160, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-cyano-7-(2-methyl-4-(6-(trifluoromethyl)pyridin-3-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.097 g, 0.190 mmol) in 2 mL of THF containing 200 μL methanol was added LiOH—H2O (0.379 mL, 0.379 mmol) and the solution was stirred at ambient temperature for 12 hours. The reaction was quenched with 1 drop of glacial acetic acid and then concentrated to dryness. The crude material was purified by silica gel column chromatography, eluting with 2-5% methanol/dichloromethane+0.1% acetic acid to provide the desired product (0.04 g, 42%). MS (APCI)=498.1 (M+1).

Workup

  1. customThe reaction was quenched with 1 drop of glacial acetic acid
  2. concentrationconcentrated to dryness
  3. customThe crude material was purified by silica gel column chromatography
  4. washeluting with 2-5% methanol/dichloromethane+0.1% acetic acid

Sources & evidence

ORD record
ord-0dd9ec519fa642c3875fce8a83507ce9
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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