Sodium Hydroxide → HCID 44601021, compound

HRID 1048139Notes

Reaction equation

HRID 1048139 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:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:33]([O:35]C)=[O:34])#[N:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20](=[O:32])[NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)=[CH:18][CH:19]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:33]([OH:35])=[O:34])#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67080778HCID 67080778, compound

Product 1

HCID 44601021HCID 44601021, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl 6-cyano-7-(4-(3-(trifluoromethyl)phenylcarbamoyl)phenoxy)chroman-4-carboxylate (0.019 g, 0.0383 mmol) in 3:1 THF/methanol (2 ml) was added 1M sodium hydroxide (0.0459 ml, 0.0459 mmol), and the reaction was stirred at ambient temperature overnight. The reaction was concentrated and partitioned between EtOAc and diluted HCl in water. The aqueous was extracted once with EtOAc, and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The crude material was purified by preparative thin layer chromatography eluting with 95:5:1 dichloromethane/methanol/acetic acid to yield 10 mg of the title compound (54.2% yield). MS (apci) m/z=480.8 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned between EtOAc and diluted HCl in water
  3. extractionThe aqueous was extracted once with EtOAc
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by preparative thin layer chromatography
  8. washeluting with 95:5:1 dichloromethane/methanol/acetic acid

Sources & evidence

ORD record
ord-fb449538c7734c9a82a0cc96633ad33d
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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