Sodium Hydroxide → HCID 15870950, compound

HRID 618054Notes

Reaction equation

HRID 618054 reaction equation
CC1(C)CC=C(C2C=C(C)C=C(C)C=2)C2C=C(C#CC3C=CC(C(OCC)=O)=CC=3)C=CC1=2.CC1(C)CC=C(C2C=CC(C)=CC=2)C2C=C(NC3C=CC=CC=3C([O-])=O)C=CC1=2.[CH3:63][C:64]1([CH3:95])[CH2:73][CH:72]=[C:71]([C:74]2[CH:79]=[CH:78][C:77]([CH3:80])=[CH:76][CH:75]=2)[C:70]2[CH:69]=[C:68]([C:81]([NH:83][C:84]3[CH:94]=[CH:93][C:87]([C:88]([O:90]CC)=[O:89])=[CH:86][CH:85]=3)=[S:82])[CH:67]=[CH:66][C:65]1=2.[OH-].[Na+]>CCO.C1COCC1>[CH3:63][C:64]1([CH3:95])[CH2:73][CH:72]=[C:71]([C:74]2[CH:79]=[CH:78][C:77]([CH3:80])=[CH:76][CH:75]=2)[C:70]2[CH:69]=[C:68]([C:81]([NH:83][C:84]3[CH:85]=[CH:86][C:87]([C:88]([OH:90])=[O:89])=[CH:93][CH:94]=3)=[S:82])[CH:67]=[CH:66][C:65]1=2

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 15870946HCID 15870946, compoundHCID 54394123HCID 54394123, compoundHCID 131721361HCID 131721361, compound

Product 1

HCID 15870950HCID 15870950, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 84.0 mg (0.184 mmol) ethyl 4[[(5,6-dihydro-5,5-dimethyl-8-(4-methylphenyl)-2-naphthalenyl]amino]-benzoate (Compound 42) in 2.0 ml EtOH and 2.0 ml of THF was added 60.0 mg NaOH (1.50 mmol, 1.5 ml of a 1M aqueous solution). After stirring at room temperature overnight, the reaction was quenched by the addition of 10% HCl. Extraction with EtOAc, and drying of the organic layers over MgSO4, provided a solid after removal of the solvent under reduced pressure. Crystallization from CH3CN afforded the title compound as a yellow solid. 1H NMR (d6-acetone): δ 10.96 (1H, s), 8.05 (4H, m), 7.72 (1H, dd, J=2.0, 8.0 Hz), 7.54 (1H, s), 7.46 (1H, d, J=8.1 Hz), 7.20 (4H, m), 6.04 (1H, t, J=4.7 Hz), 2.38 (2H, d, J=4.7 Hz), 2.33 (3H, s), 1.35 (6H, s).

Workup

  1. customthe reaction was quenched by the addition of 10% HCl
  2. extractionExtraction with EtOAc
  3. dry with materialdrying of the organic layers over MgSO4
  4. customprovided a solid
  5. customafter removal of the solvent under reduced pressure
  6. customCrystallization from CH3CN

Sources & evidence

ORD record
ord-c292758aec35477e829d82df1036e0d6
Source dataset
uspto-grants-1999_09
Patent number
US05952345

Reaction notes

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