Ethyl 4-methoxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetate → [4-Methoxy-1-methyl-5-(2-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid

HRID 1388931

Reaction equation

HRID 1388931 reaction equation
COC1C(C(OCC)=O)=C(CC(OCC)=O)N(C)C=1.[CH3:20][C:21]1[CH:45]=[CH:44][CH:43]=[CH:42][C:22]=1[C:23]([C:25]1[N:29]([CH3:30])[C:28]([CH2:31][C:32]([O-:34])=[O:33])=[C:27](C(OCC)=O)[C:26]=1[O:40][CH3:41])=[O:24].CC1C=CC=CC=1C(C1N(C)C(CC(O)=O)=C(C(O)=O)C=1OC)=O>C(O)(C(F)(F)F)=O>[CH3:20][C:21]1[CH:45]=[CH:44][CH:43]=[CH:42][C:22]=1[C:23]([C:25]1[N:29]([CH3:30])[C:28]([CH2:31][C:32]([OH:34])=[O:33])=[CH:27][C:26]=1[O:40][CH3:41])=[O:24]

Participants

5

Reactant 3

HCID 20469092Ethyl 4-methoxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetateHCID 204691135-(o-Methylbenzoyl)-4-methoxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetateHCID 204691545-(o-Methylbenzoyl)-4-methoxy-3-hydroxycarbonyl-1-methylpyrrole-2-acetic acid

Product 1

HCID 20469089[4-Methoxy-1-methyl-5-(2-methylbenzoyl)-1H-pyrrol-2-yl]acetic acidYield 50%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Following substantially the procedures as described in Example 1, Steps C-E, crude ethyl 4-methoxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetate is converted to about 16 mmole of 5-(o-methylbenzoyl)-4-methoxy-3-ethoxycarbonyl-1-methylpyrrole-2-acetate followed by hydrolysis to 5-(o-methylbenzoyl)-4-methoxy-3-hydroxycarbonyl-1-methylpyrrole-2-acetic acid which in turn is decarboxylated in neat TFA according to procedure of Example 2 to afford an overall 50% yield of 5-(o-methylbenzoyl)-4-methoxy-1-methylpyrrole-2-acetic acid.

Sources & evidence

ORD record
ord-96574269ed3d4b2091a51409e088389a
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Linked notes

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