Hydrochloric Acid → HCID 67080881, compound

HRID 510703Notes

Reaction equation

HRID 510703 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][NH:12][C:13]([C:15]3[CH:37]=[CH:36][C:18]([O:19][C:20]4[CH:29]=[C:28]5[C:23]([CH:24]([C:30]([O:32]CC)=[O:31])[CH2:25][CH2:26][O:27]5)=[CH:22][C:21]=4[Cl:35])=[CH:17][CH:16]=3)=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[Na+].Cl>O1CCCC1CCO.C(OCC)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][NH:12][C:13]([C:15]3[CH:37]=[CH:36][C:18]([O:19][C:20]4[CH:29]=[C:28]5[C:23]([CH:24]([C:30]([OH:32])=[O:31])[CH2:25][CH2:26][O:27]5)=[CH:22][C:21]=4[Cl:35])=[CH:17][CH:16]=3)=[O:14])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67081552HCID 67081552, compound

Product 1

HCID 67080881HCID 67080881, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

Ethyl 7-(4-(2-(benzo[d][1,3]dioxol-5-yl)ethylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (65 mg, 0.124 mmol) was dissolved in 2:1 tetrahydrofuran-ethanol and treated with 1.0 molar sodium hydroxide (496 μl, 0.496 mmol) at ambient temperature. After 3 hours, the reaction was diluted with ethyl acetate, neutralized with 1.0 molar hydrochloric acid (521 μl, 0.521 mmol), and partitioned between saturated sodium chloride aqueous solution. The organic layer was dried with sodium sulfate, filtered, concentrated, and dried under high vacuum to provide the title compound (61 mg, 0.123 mmol, 99.2% yield) as a solid.

Workup

  1. custompartitioned between saturated sodium chloride aqueous solution
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-60ea76d7655c495fa38a36508d78ec2f
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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