Methanol → HCID 67287832, compound

HRID 1626484Notes

Reaction equation

HRID 1626484 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:33])[NH:21][C:22]3[S:23][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[N:25][N:26]=3)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:34]([O:36]C)=[O:35])#[N:2].[OH-].[Na+].CO>C1COCC1.C(OCC)(=O)C.Cl>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20](=[O:33])[NH:21][C:22]3[S:23][C:24]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[N:25][N:26]=3)=[CH:18][CH:19]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:34]([OH:36])=[O:35])#[N:2]

Participants

7

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67287755HCID 67287755, compound

Product 1

HCID 67287832HCID 67287832, compoundYield 60.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 6-cyano-7-(4-(5-phenyl-1,3,4-thiadiazol-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (17 mg, 0.033 mmol) was diluted with THF (500 μL) followed by the addition of NaOH (166 μL, 0.17 mmol) and methanol (200 μL). After stirring for 2 hours, the reaction was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield 6-cyano-7-(4-(5-phenyl-1,3,4-thiadiazol-2-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid (10 mg, 0.020 mmol, 60% yield). MS (APCI)=498.9 (M+1).

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-1f33ef5a28b7422eb89565c8cbb1caf2
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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