methyl 5-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate → 3-[5-(methoxycarbonyl)-1H-pyrrol-2-yl]propanoic acid

HRID 601793Notes

Reaction equation

HRID 601793 reaction equation
C([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[NH:13][C:12]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:10]=1)(C)(C)C>Cl>[CH3:17][O:16][C:14]([C:12]1[NH:13][C:9]([CH2:8][CH2:7][C:6]([OH:18])=[O:5])=[CH:10][CH:11]=1)=[O:15]

Participants

3

Reactant 1

HCID 66873239methyl 5-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 668739873-[5-(methoxycarbonyl)-1H-pyrrol-2-yl]propanoic acidYield 111.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl 5-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate (14.8 g, 58.4 mmol) was treated with 4 N HCl (100 mL) at rt for about 12 h. The solvent was removed and the white solid product was dried to give 12.8 g (94%) of 3-(5-(methoxycarbonyl)-1H-pyrrol-2-yl)propanoic acid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.73 (t, J=6.81 Hz, 2H), 2.98 (t, J=6.79 Hz, 2H), 3.83 (s, 3H), 6.01 (dd, J=3.59, 2.61 Hz, 1H), 6.83 (dd, J=3.61, 2.63 Hz, 1H), 9.70 (br s, 1H); LCMS-MS (ESI+) 198.2 (M+H).

Workup

  1. customThe solvent was removed
  2. customthe white solid product was dried

Sources & evidence

ORD record
ord-fc9c7f0f3bfe4f9d98f8478fec6a5746
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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