Sodium Hydroxide → HCID 22613066, compound

HRID 844362Notes

Reaction equation

HRID 844362 reaction equation
C([O:3][C:4](=[O:28])[C:5](=[O:27])[CH2:6][C:7]([C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:12]=[C:11]([O:23][CH3:24])[C:10]=1[O:25][CH3:26])=[O:8])C.[OH-].[Na+]>CO.CC(O)=O.C(Cl)Cl>[F:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C:13]2[CH:12]=[C:11]([O:23][CH3:24])[C:10]([O:25][CH3:26])=[C:9]([C:7](=[O:8])[CH2:6][C:5](=[O:27])[C:4]([OH:28])=[O:3])[CH:14]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69945020HCID 69945020, compound

Product 1

HCID 22613066HCID 22613066, compound

Reagents, catalysts & solvents 1

HCID 21877243DCM MeOH AcOHSolvent

Procedure

In a manner similar to example AIV-2-1, 4-[5-(4-fluoro-benzyl)-2,3-dimethoxy-phenyl]-2,4-dioxo-butyric acid ethyl ester was formed and the crude material was hydrolyzed in a manner similar to example AIV-3-1 using 1N NaOH to afford L3 as a yellow solid. Rf=0.67 (6:6:94 MeOH/AcOH/CH2Cl2). 1H NMR (400 MHz, CDCl3) δ7.38 (s, 1H), 7.25 (m, 1H), 7.14 (m, 2H), 7.00 (m, 2H), 6.88 (m, 1H), 3.94 (s, 2H), 3.90 (s, 3H), 3.85 (s, 3H). mass spec (FAB, M+1) 361 m/e.

Workup

  1. customto afford L3 as a yellow solid

Sources & evidence

ORD record
ord-64b31386583c42da80f16ebd752079ee
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

Loading…