Sodium Hydroxide → HCID 67287480, compound

HRID 1626435Notes

Reaction equation

HRID 1626435 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][C:30]([CH3:33])=[CH:29][CH:28]=4)[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: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:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=4)[N:22]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([OH:37])=[O:36]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67287963HCID 67287963, compound

Product 1

HCID 67287480HCID 67287480, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of ethyl 6-chloro-7-(4-(6-p-tolylpyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.049 g, 0.090 mmol) in 3:1 THF/ethanol (1 ml) was added 1M sodium hydroxide (0.19 ml, 0.19 mmol), and the reaction was stirred at ambient temperature for 16 hours. The reaction was concentrated to dryness and acidified with 1M hydrochloric acid. The reaction was diluted with water and extracted twice with EtOAc. The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to yield the desired compound (0.035 g, 0.068 mmol, 75% yield). MS (apci) m/z=515.1 (M+H).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. additionThe reaction was diluted with water
  3. extractionextracted twice with EtOAc
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cfa8541386434a7b83a978943db5111f
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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