Methanol → HCID 59730322, compound

HRID 131037Notes

Reaction equation

HRID 131037 reaction equation
C([O:3][C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][N:19]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:14][CH:13]=2)=[N:7][CH:6]=1)C.CO.[OH-].[Na+]>C1COCC1>[C:31]([O:30][C:28]([N:19]([CH2:18][C:15]1[CH:14]=[CH:13][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:35])=[O:3])=[CH:6][N:7]=2)=[CH:17][CH:16]=1)[CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59730398HCID 59730398, compound

Product 1

HCID 59730322HCID 59730322, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 6-{4-[(tert-Butoxycarbonyl-phenethyl-amino)-methyl]-phenoxy}-nicotinic acid ethyl ester (0.333 g, 0.72 mmol), MeOH (5 mL), THF (5 mL), and 2.5N NaOH (aq) (2 mL). After the reaction refluxes under a Nitrogen atmosphere for 24 hours, concentrate under reduced pressure. Add 2.5N HCl (aq) (2 mL), Ethyl acetate, and wash with water, brine, and then dry over Na2SO4. Concentrate the organic mixture under reduced pressure to afford 293.0 mg (91% yield) of title compound as a white foam: 1H NMR (500 MHz, CDCl3); 1.4 (9H, s), 2.6-2.8 (2H, m), 3.2-3.4 (2H, m), 4.2-4.4 (2H, m), 4.3-4.4 (2H, m), 6.9 (1H, d), 7.0-7.3 (9H, m), 8.3 (1H, d), 8.8 (1H, s); MS m/z 349 (M−100, Boc).

Workup

  1. concentrationconcentrate under reduced pressure
  2. additionAdd 2.5N HCl (aq) (2 mL), Ethyl acetate
  3. washwash with water, brine
  4. dry with materialdry over Na2SO4
  5. concentrationConcentrate the organic mixture under reduced pressure

Sources & evidence

ORD record
ord-305e647d191a47c1a39e4414b9fa3e2d
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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