Sodium Hydroxide → HCID 44599428, compound

HRID 510799Notes

Reaction equation

HRID 510799 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[C:35]([CH:37]2[CH2:39][CH2:38]2)[CH:34]=[CH:33][C:4]=1[CH2:5][CH2:6][NH:7][C:8]([C:10]1[CH:32]=[CH:31][C:13]([O:14][C:15]2[CH:24]=[C:23]3[C:18]([CH:19]([C:25]([O:27]CC)=[O:26])[CH2:20][CH2:21][O:22]3)=[CH:17][C:16]=2[Cl:30])=[CH:12][CH:11]=1)=[O:9].[OH-].[Na+]>C1COCC1.C(O)C.CCOC(C)=O.Cl>[Cl:30][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:15]=1[O:14][C:13]1[CH:31]=[CH:32][C:10]([C:8](=[O:9])[NH:7][CH2:6][CH2:5][C:4]3[CH:33]=[CH:34][C:35]([CH:37]4[CH2:39][CH2:38]4)=[CH:36][C:3]=3[O:2][CH3:1])=[CH:11][CH:12]=1)[O:22][CH2:21][CH2:20][CH:19]2[C:25]([OH:27])=[O:26]

Participants

7

Reactant 2

HCID 14798Sodium HydroxideHCID 67081068HCID 67081068, compound

Product 1

HCID 44599428HCID 44599428, compoundYield 89.3%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 7-(4-(2-methoxy-4-cyclopropylphenethylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (0.07 g; 0.133 mmol) in a mixture of 1.2 mL THF and 0.6 mL ethanol at ambient temperature was added 0.53 mL of 1M aqueous NaOH. The resulting slightly cloudy mixture was vigorously stirred at ambient temperature. After 1 hour the reaction mixture was diluted with 6 mL EtOAc and 3 mL of 1M aqueous HCl, then transferred to a separatory funnel. After shaking, the organic layer was washed with 2 mL brine, then dried over sodium sulfate and evaporated to give 62 mg of 6-chloro-7-(4-(4-cyclopropyl-2-methoxyphenethylcarbamoyl)phenoxy)chroman-4-carboxylic acid as a colorless oil. MS (apci, pos) m/z=523.

Workup

  1. customtransferred to a separatory funnel
  2. stirringAfter shaking
  3. washthe organic layer was washed with 2 mL brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-b8a6c64968d3455cade3378992ba2537
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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