Potassium Hydroxide → HCID 22237562, compound

HRID 324095Notes

Reaction equation

HRID 324095 reaction equation
C([O:3][C:4](=[O:47])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[C:14]([C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=2)=[CH:13][C:12]([C:23](=[O:38])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:11][C:10]=1[C:39]1[CH:44]=[C:43]([CH3:45])[CH:42]=[C:41]([CH3:46])[CH:40]=1)C.[OH-].[K+]>CO.Cl.O>[CH3:22][C:17]1[CH:16]=[C:15]([C:14]2[CH:13]=[C:12]([C:23](=[O:38])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:11]=[C:10]([C:39]3[CH:44]=[C:43]([CH3:45])[CH:42]=[C:41]([CH3:46])[CH:40]=3)[C:9]=2[O:8][CH2:7][CH2:6][CH2:5][C:4]([OH:47])=[O:3])[CH:20]=[C:19]([CH3:21])[CH:18]=1

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 69628639HCID 69628639, compound

Product 1

HCID 22237562HCID 22237562, compoundYield 45.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4-[3,5,3″,5″-Tetramethyl-5′-(7-phenyl-heptylcarbamoyl)-[1,1′:3′,1″]terphenyl-2′-yloxy]-butyric acid ethyl ester (170 mg, 0.256 mmol) in 4 mL MeOH/1 mL H2O was added solid KOH (12 mg, 0.213 mmol). The reaction mixture was refluxed for 2 d and then the reaction mixture was diluted with 2N HCl and water. The aqueous solution was extracted with EtOAc (3×) and the combined organic extracts were dried over Na2SO4. The solvent was removed in vacuo to give an oil that was flash chromatographed (10% EtOAc:90% Hexanes) on silica gel to yield 70 mg, 43% of the acid as an oily white foam. mp 64-66″C; 1H NMR (DMSO-d6) δ1.29-1.30 (m, 6H); 1.32-1.39 (m, 2H); 1.46-1.48 (m, 4H); 1.86 (t, J=7.47 Hz, 2H); 2.33 (s, 12H); 2.53 (t, J=7.58 Hz, 2H); 3.19-3.31 (m, 4H); 7.01 (s, 2H); 7.12-7.16 (m, 3H); 7.17-7.19 (m, 4H); 7.21-7.24 (m, 2H) 7.71 (s, 2H); 8.48 (t, J=7.00 Hz, 1H); 11.86 (s, 1H); IR 3325, 2925, 2875, 1710, 1630, 1600, 1535, 1450, 1290, 1225, 1210, 850, and 700 cm−1; mass spectrum [(+)APCI], m/z 606 [M+H]+; Anal Calcd. for C40H47NO4: C, 79.30; H, 7.82; N, 2.31; Found: C, 78.65; H, 7.86; N, 1.87.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 d
  2. extractionThe aqueous solution was extracted with EtOAc (3×)
  3. dry with materialthe combined organic extracts were dried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. customto give an oil that
  6. customchromatographed (10% EtOAc:90% Hexanes) on silica gel

Sources & evidence

ORD record
ord-7d5b7a7040e049f698c353a24b7060b0
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Reaction notes

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