Hydrochloric Acid → 3-(5-(methoxycarbonyl)-1H-pyrrol-3-yl)propanoic acid

HRID 601896Notes

Reaction equation

HRID 601896 reaction equation
C([O:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[NH:12][CH:13]=1)(C)(C)C.Cl>>[CH3:17][O:16][C:14]([C:11]1[NH:12][CH:13]=[C:9]([CH2:8][CH2:7][C:6]([OH:18])=[O:5])[CH:10]=1)=[O:15]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 59180142methyl 4-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 591801963-(5-(methoxycarbonyl)-1H-pyrrol-3-yl)propanoic acidYield 95%

Procedure

Methyl 4-(3-tert-butoxy-3-oxopropyl)-1H-pyrrole-2-carboxylate (473 g, 1.87 mmol) was treated for about 12 h at rt with 4 N HCl (5 mL). The solvent was removed and the white solid product was dried to give 350 mg (95%) of 3-(5-(methoxycarbonyl)-1H-pyrrol-3-yl)propanoic acid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.64 (t, J=7.35 Hz, 2H), 2.84 (t, J=7.35 Hz, 2H), 3.85 (s, 3H), 6.79 (dd, J=6.66, 2.22 Hz, 2H), 9.08 (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-1c6fe79713664b52a36cf4ce1e3225d1
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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