Methanol → 6-Cyano-7-(4-(phenethylcarbamoyl)phenoxy) chroman-4-carboxylic acid

HRID 510609Notes

Reaction equation

HRID 510609 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:30])[NH:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:16][CH:15]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:31]([O:33]C)=[O:32])#[N:2].[OH-].[Na+].O.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:30])[NH:21][CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:18][CH:19]=1)[O:9][CH2:8][CH2:7][CH:6]2[C:31]([OH:33])=[O:32])#[N:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67080237HCID 67080237, compound

Product 1

HCID 670801446-Cyano-7-(4-(phenethylcarbamoyl)phenoxy) chroman-4-carboxylic acidYield 76.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 6-cyano-7-(4-(phenethylcarbamoyl)phenoxy)chroman-4-carboxylate (16.1 mg, 0.0353 mmol) was diluted with THF (500 μL) followed by the addition of NaOH (0.0705 mL, 0.353 mmol) and water (100 μL) and methanol (100 μL). After stirring for 3 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 the title compound (12.0 mg, 76.9% yield). 1H NMR (400 MHz, CD3OD) δ □7.85 (d, 2H), 7.66 (s, 1H), 7.20-7.30 (m, 5H), 7.15 (d, 2H), 6.40 (s, 1H), 4.20-4.35 (m, 2H), 3.85 (bt, 1H), 3.58 (t, 2H), 2.92 (t, 2H), 2.3-2.4 (m, 1H), 2.1-2.2 (m, 1H).

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-326d00e37593455db10ff3abe99a8ac9
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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