1H-Pyrrole-2-carboxylicacid,3-hydroxy-,methylester(9CI)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 3-hydroxy-1H-pyrrole-2-carboxylate (2.0 g, 0.014 moles) is dissolved in DMF (15 mL) under nitrogen. Potassium carbonate (2.8 g, 0.020 moles) is added followed by 2-bromopropane (5 mL, 0.05 moles) and the mixture is stirred at room temperature for 18 hours, then at 50° C. for 3 hours, then stirred into ice water (400 mL). The mixture is extracted with CH2Cl2 (3x) and the combined extracts are washed with brine (2x) and dried over MgSO4. Removal of the solvent under reduced pressure leaves the crude product as a crystalline residue. Recrystallization from ether gave the pure product (1.6 g); mp 77°-79° C. at 50° C. for 3 hours The mixture is extracted with CH2Cl2 (3x) the combined extracts are washed with brine (2x) dried over MgSO4 Removal of the solvent under reduced pressure leaves the crude product as a crystalline residue Recrystallization from ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 3-hydroxy-1H-pyrrole-2-carboxylate (2.0 g, 0.014 moles) is dissolved in DMF (15 mL) under nitrogen. Potassium carbonate (2.8 g, 0.020 moles) is added followed by 2-bromopropane (5 mL, 0.05 moles) and the mixture is stirred at room temperature for 18 hours, then at 50° C. for 3 hours, then stirred into ice water (400 mL). The mixture is extracted with CH2Cl2 (3x) and the combined extracts are washed with brine (2x) and dried over MgSO4. Removal of the solvent under reduced pressure leaves the crude product as a crystalline residue. Recrystallization from ether gave the pure product (1.6 g); mp 77°-79° C. at 50° C. for 3 hours The mixture is extracted with CH2Cl2 (3x) the combined extracts are washed with brine (2x) dried over MgSO4 Removal of the solvent under reduced pressure leaves the crude product as a crystalline residue Recrystallization from ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared by the method described in Example 101 from methyl glycinate (22 g, 0.25 moles), methyl α-chloroacrylate (29.8 g, 0.25 moles), and sodium (17 g, 0.74 moles). Following filtration through silica gel and evaporation of the filtrate, the product is obtained pure and crystalline (18.6 g ; mp 100°-102° C. Prepared by the method filtration through silica gel and evaporation of the filtrate the product is obtained pure

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Diisopropylethylamine (7.1 mL, 40.7 mmole) and then a solution of TsCl (6.46 gm, 33.9 mole) in dry DCM (20 mL) were added to an ice-cooled solution of methyl 3-hydroxy-1H-pyrrole-2-carboxylate (4.78 gm; 33.9 mmole) in dry DCM (80 mL) under a dry N2 atmosphere. After 2 hr, the reaction was removed from the bath and allowed to warm to RT. After 2 hr, this was washed with water, dried (Na2SO4), and the solvents removed to leave methyl 3-(tosyloxy)-1H-pyrrole-2-carboxylate (10 gm) as a solid. 1H NMR (CDCl3): 2.39 (s, 3H), 3.64 (s, 3H), 6.06 (m, 1H), 6.75 (m, 1H), 7.26 (m, 2H), 7.71 (m, 2H); MS: 311(M+H)+; HPLC Ret Time: 1.28 min (YMC Xterra S7 3.0×50 mm column, 2 min gradient, 5 mL/min). the reaction was removed from the bath After 2 hr this was washed with water dried (Na2SO4) the solvents removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 3-hydroxy-1H-pyrrole-2-carboxylate (2.0 g, 0.014 moles) is dissolved in DMF (15 mL) under nitrogen. Potassium carbonate (2.8 g, 0.020 moles) is added followed by 2-bromopropane (5 mL, 0.05 moles) and the mixture is stirred at room temperature for 18 hours, then at 50° C. for 3 hours, then stirred into ice water (400 mL). The mixture is extracted with CH2Cl2 (3x) and the combined extracts are washed with brine (2x) and dried over MgSO4. Removal of the solvent under reduced pressure leaves the crude product as a crystalline residue. Recrystallization from ether gave the pure product (1.6 g); mp 77°-79° C. at 50° C. for 3 hours The mixture is extracted with CH2Cl2 (3x) the combined extracts are washed with brine (2x) dried over MgSO4 Removal of the solvent under reduced pressure leaves the crude product as a crystalline residue Recrystallization from ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared by the method described in Example 101 from methyl glycinate (22 g, 0.25 moles), methyl α-chloroacrylate (29.8 g, 0.25 moles), and sodium (17 g, 0.74 moles). Following filtration through silica gel and evaporation of the filtrate, the product is obtained pure and crystalline (18.6 g ; mp 100°-102° C. Prepared by the method filtration through silica gel and evaporation of the filtrate the product is obtained pure