Sodium Hydroxide → HCID 67288232, compound

HRID 1626432Notes

Reaction equation

HRID 1626432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:34])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[N:22]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([O:37]CC)=[O:36].[OH-].[Na+]>C1COCC1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:34])[NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[N:22]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([OH:37])=[O:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67289647HCID 67289647, compound

Product 1

HCID 67288232HCID 67288232, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of ethyl 6-chloro-7-(4-(6-(2-chlorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.010 g, 0.0177 mmol) in 3:1 THF/ethanol (1 ml) was added 1M sodium hydroxide (0.0373 ml, 0.0373 mmol), and the reaction was stirred for 16 hours at ambient temperature. The reaction was concentrated and diluted with water. The reaction was acidified with 1M hydrochloric acid and extracted twice with EtOAc. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by silica gel preparative thin-layer chromatography eluting with 95:5:1 DCM/MeOH/glacial acetic acid to yield the desired compound (0.007 g, 0.0124 mmol, 70.0% yield). MS (apci) m/z=535.1 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with water
  3. extractionextracted twice with EtOAc
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel preparative thin-layer chromatography
  8. washeluting with 95:5:1 DCM/MeOH/glacial acetic acid

Sources & evidence

ORD record
ord-c936bd3a07794d80a0909a25a386556f
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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