Ethanol → HCID 67288774, compound

HRID 1626466Notes

Reaction equation

HRID 1626466 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][C:24]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)=[CH:23][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+].C(O)C>C1COCC1.C(OCC)(=O)C.Cl>[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][C:24]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)=[CH:23][N:22]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:35]([OH:37])=[O:36]

Participants

7

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67289726HCID 67289726, compound

Product 1

HCID 67288774HCID 67288774, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 6-chloro-7-(4-(5-(4-chlorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (30 mg, 0.053 mmol) was diluted with THF (500 μL) followed by the addition of NaOH (266 μl, 0.27 mmol) and ethanol (200 μL). After stirring for 2 hours, the reaction was diluted with ethyl acetate and 0.5N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield the desired compound (27 mg, 0.050 mmol, 95% yield). MS (ESI)=535.1 (M+H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2e2d5a7178444339a1fafa867171012e
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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