Hydrochloric Acid → 2-Methyl-5-(2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl)-furan-3-carboxylic acid

HRID 1944257Notes

Reaction equation

HRID 1944257 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:31])[CH2:18][C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)=[CH:12][C:11]=2[N+:32]([O-:34])=[O:33])[O:7][C:6]=1[CH3:35])=[O:4].[Li+].[OH-].Cl>C1COCC1.CO.CCOC(C)=O>[CH3:35][C:6]1[O:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:31])[CH2:18][C:19]3[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][CH3:28])=[C:21]([O:29][CH3:30])[CH:20]=3)=[CH:12][C:11]=2[N+:32]([O-:34])=[O:33])=[CH:9][C:5]=1[C:3]([OH:4])=[O:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 597857112-Methyl-5-{2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid methyl ester

Product 1

HCID 597857142-Methyl-5-(2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl)-furan-3-carboxylic acidYield 74.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2-Methyl-5-{2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid methyl ester (41) (50 mg, 0.10 mmol) in THF (1.0 mL) and MeOH (0.5 mL) at rt and add 1M aqu LiOH (525 μL, 0.52 mmol). Stir the reaction mixture for 17 h at rt. Add dropwise 1M aqu. HCl (580 μL, 0.58 mmol) and extract the mixture with EtOAc (3 times), wash the combined organic layer with brine and dry it with Na2SO4. Purify the obtained crude product by preparative TLC (silica gel, EtOAc/MeOH 9+1) to obtain 2-Methyl-5-(2-nitro-4-[2-(3,4,5-trimethoxy-phenyl)-acetylamino]-phenyl)-furan-3-carboxylic acid (42) (35 mg, 71%) as a brown sticky solid. 1H NMR (400 MHz, CDCl3): 2.61 (s, 3H); 3.70 (s, 2H); 3.86 (s, 3H); 3.87 (s, 6H); 6.51 (s, 2H); 6.85 (s, 1H); 7.29 (br.s, 1H); 7.58 (d, 1H, J=8.6 Hz); 7.62 (dd, 1H, J1=9.0 Hz, J2=2.2 Hz); 7.98 (d, 1H, J=2.0 Hz).

Workup

  1. additionAdd dropwise 1M aqu
  2. washwash the combined organic layer with brine
  3. dry with materialdry it with Na2SO4
  4. customPurify the
  5. customobtained crude product by preparative TLC (silica gel, EtOAc/MeOH 9+1)

Sources & evidence

ORD record
ord-2fbbbc2652f64d50ba2eb6b1846f6efd
Source dataset
uspto-grants-2013_03
Patent number
US08394835B2

Reaction notes

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