methyl 4-hydroxybut-2-ynoate

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

Procedure: The desired compound was prepared according to the method of Example 1, step 3, except substituting 4,4-bis(2-quinolylmethoxy)phenyl)-4-hydroxy-2-butynoic acid methyl ester, prepared as in step 1, for 4,4-bis(4-(2-quinolylmethoxy)phenyl)-pentanoic acid: mp 169°-172° C.; 1H NMR (300 MHz, DMSO--d6) d 5.35 (s, 4H), 7.04 (d, 4H, J=9 Hz), 7.37 (d, 4H, J=9 Hz), 7.63 (m, 4H), 7.78 (m, 2H), 8.00 (m, 4H), 8.40 (d, 2H, J=8 Hz), 13.75 (bs, 1H); MS (DCI--NH3) m/e: 567 (M+H)+. Anal. Calc'd. for C36H26 N2O4. 0.5 H2O: C, 75.12; H, 4.73;N, 4.89. Found: 75.19; H, 4.80; N, 4.60.

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

Procedure: 0.41 ml of boron trifluoride etherate was added to a suspension of 4.70 g (25 mmols) of (1R, 5S)-3-phenyl-4-oxa-2,6-diazabicyclo[3.2.0]hept-2-en-7-one and 14.3 g (125 mmols--5 equivalents) of methyl 4-hydroxy-2-butinoate (R. A. Earl, Organic Synthese 60, 81) in 40 ml of anhydrous methylene chloride at room temperature. The mixture was stirred at room temperature for 1 hour, whereupon a clear solution formed. The solution was then poured into dilute NaHCO3 solution, the mixture was extracted with methylene chloride and the extracts were washed with water and dried over MgSO4. After the solvent had been evaporated off in vacuo and the residue had been filtered on 120 g of silica gel (toluene:ethyl acetate 2:3), 4.74 g (63%) of methyl 4-[3(R)-benzoylamino-2-azetidinon-4(R)-yloxy]-2-butinoate were obtained as colorless crystals, melting point: 142°-143° C, RF : 0.29 (toluene:ethyl acetate 2:3), [α]D20 =18.37° (1.0345 percent in acetone). at room temperature formed the mixture was extracted with methylene chloride the extracts were washed with water dried over MgSO4 After the solvent had been evaporated off in vacuo the residue had been filtered on 120 g of silica gel (toluene:ethyl acetate 2:3)

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

Procedure: The desired compound was prepared according to the method of Example 1, step 3, except substituting 4,4-bis(2-quinolylmethoxy)phenyl)-4-hydroxy-2-butynoic acid methyl ester, prepared as in step 1, for 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentanoic acid: mp 169°-172° C.; 1H NMR (300 MHz, DMSO-d6) d 5.35 (s, 4H), 7.04 (d, 4H, J=9 Hz), 7.37 (d, 4H, J=9 Hz), 7.63 (m, 4H), 7.78 (m, 2H), 8.00 (m, 4H), 8.40 (d, 2H, J=8 Hz), 13.75 (bs, 1H); MS (DCl--NH3) m/e: 567 (M+H)+. Anal. Calc'd. for C36H26 N2O4.0.5 H2O: C, 75.12; H, 4.73; N, 4.89. Found: 75.19; H, 4.80; N, 4.60.

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

Procedure: The desired compound was prepared according to the method of Example 1, step 3, except substituting 4,4-bis(2-quinolylmethoxy)phenyl)-4-hydroxy-2-butynoic acid methyl ester, prepared as in step 1, for 4,4-bis(4-(2-quinolylmethoxy)phenyl)-pentanoic acid: mp 169°-172° C.; 1H NMR (300 MHz, DMSO--d6) d 5.35 (s, 4H), 7.04 (d, 4H, J=9 Hz), 7.37 (d, 4H, J=9 Hz), 7.63 (m, 4H), 7.78 (m, 2H), 8.00 (m, 4H), 8.40 (d, 2H, J=8 Hz), 13.75 (bs, 1H); MS (DCI--NH3) m/e: 567 (M+H)+. Anal. Calc'd. for C36H26 N2O4. 0.5 H2O: C, 75.12; H, 4.73;N, 4.89. Found: 75.19; H, 4.80; N, 4.60.