Acetic Acid → HCID 2801523, compound

HRID 1507688Notes

Reaction equation

HRID 1507688 reaction equation
[C:1](OCC)(=[O:7])[C:2](OCC)=[O:3].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][CH:14]=1.CC[O-].[Na+].C(O)(=O)C>O>[OH:3][C:2]1[C:1]([OH:7])=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 86134692HCID 86134692, compound

Product 1

HCID 2801523HCID 2801523, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Diethyl oxalate (83 ml, 0.61 mol) was added dropwise to a stirred solution of diethyl 2,2′4-(4-methoxyphenyl)azanediyl)diacetate (4) (180 g, 0.61 mol) in NaOEt (21% by wt in EtOH) (506 ml, 1.3 mol), the mixture was stirred at 100° C. for 1 h. The reaction was quenched with acetic acid (210 ml, 3.7 mol) and the resulting suspension was poured into iced water (1 L), the resulting off-white solid collected by vacuum filtration. The crude product was recrystallised from hot EtOH (3.5 L) to give diethyl 3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylate (UL2-001) (152 g, 71%) as a white solid: m/z 350 (M+H)+ (ES+); 348 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ 8.64 (s, 2H), 7.13-7.01 (m, 2H), 6.92-6.81 (m, 2H), 3.99 (q, J=7.1 Hz, 4H), 3.78 (s, 3H), 0.99 (t, J=7.1 Hz, 6H).

Workup

  1. filtrationthe resulting off-white solid collected by vacuum filtration
  2. customThe crude product was recrystallised from hot EtOH (3.5 L)

Sources & evidence

ORD record
ord-238206118b264ab7b1dd0642138a8fea
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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