Methanol → HCID 23690851, compound

HRID 1456857Notes

Reaction equation

HRID 1456857 reaction equation
CO.[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=3)=[CH:30][CH:29]=2)([CH3:27])[CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:17][CH:16]=1.[OH-].[Na+:47]>O1CCOCC1>[Na+:47].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=3)=[CH:30][CH:29]=2)([CH3:27])[CH2:22][CH2:23][C:24]([O-:26])=[O:25])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 9850972HCID 9850972, compound

Product 1

HCID 23690851HCID 23690851, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution in dioxane (10 mL) and methanol (10 mL) of 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentanoic acid (320 mg, 0.56 mmol), prepared as in step 1, was added aqueous 1N sodium hydroxide (0.55 ml, 0.55 mmol). The mixture was then concentrated in vacuo. The product was crystallized by dissolving in CH2Cl2 and precipitation by dropwise addition of a mixture of ethyl acetate-ethyl ether (1:2): 1 H NMR (300 MHz, DMSO-d6) d 1.47 (s, 3H), 1.63 (m, 2H), 2.18 (m, 2H), 5.31 (s, 4H), 6.95 (d, 4H, J=9 Hz), 7.08 (d, 4H, J=9 Hz), 7.64 (m, 4H), 7.78 (m, 2H), 8.00 (m, 4H), 8.40 (d, 2H, J=8 Hz); MS (FAB+) m/e 591 (M+H)+ ; (FAB-) 589 (M-H)-. Anal. Calc'd. for C37 H31N2O4Na.0.25 H2O:C, 74.67; H, 5.34; N, 4.71; Found: C, 74.57; H, 5.32; N, 4.52.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe product was crystallized
  3. dissolutionby dissolving in CH2Cl2
  4. customprecipitation
  5. additionby dropwise addition of a mixture of ethyl acetate-ethyl ether (1:2)

Sources & evidence

ORD record
ord-ae9ae6607d4947baa35de5b898e0b88d
Source dataset
uspto-grants-1998_12
Patent number
US05843968

Reaction notes

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