heptanedioyl dichloride

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

Procedure: To a stirred solution of (4R)-2-(3-nitrophenyl-4-thiazolidinecarboxylic acid (5.1 g) in 1M sodium carbonate (40 ml), heptanedioyl dichloride (2.1 g) was added dropwise under ice-cooling. The reaction mixture was stirred for 1 hour at the same temperature, and the separated crystals were filtered to give 4.7 g (69%) of the titled compound as disodium salt: mp 111°-113° C. (dec.) (water); [α]D25 +88.2° (c=0.5, methanol). IR (nujol, cm-1): 1635 (CON), 1585 (COO-), 1520 and 1355 (NO2), 1095, 730. TLC: Rf value* 0.28. cooling the separated crystals were filtered

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

Procedure: To a stirred solution of (4R)-2-(3-nitrophenyl-4-thiazolidinecarboxylic acid (5.1 g) in 1M sodium carbonate (40 ml), heptanedioyl dichloride (2.1 g) was added dropwise under ice-cooling. The reaction mixture was stirred for 1 hour at the same temperature, and the separated crystals were filtered to give 4.7 g (69%) of the titled compound as disodium salt: mp 111°-113° C. (dec.) (water); [α]D25 +88.2° (c=0.5, methanol). IR (nujol, cm-1): 1635 (CON), 1585 (COO-), 1520 and 1355 (NO2), 1095, 730. TLC: Rf value* 0.28. cooling the separated crystals were filtered

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

Procedure: To a stirred solution of (4R)-2-(3-cyanophenyl)-4-thiazolidinecarboxylic acid (4.7 g) in 1M sodium carbonate (30 ml), heptanedioyl dichloride (2.1 g) was added dropwise under ice-cooling. The reaction mixture was stirred for 30 minutes at the same temperature, and filtered to give the precipitates. The precipitates were dissolved in hot water (100 ml), and acidified with concentrated hydrochloric acid. The separated crystals were collected by filtration to give 3.5 g (59%) of the titled compound: mp 105°-112° C.; [α]D25 +115.0° (c=1.0, methanol). IR (nujol, cm-1): 2270 (CN), 1735 (COOH), 1640 (CON), 1610 (aromatic), 1195, 790 (aromatic). NMR (DMSO-d6) δ: 0.69-1.66 (6H, m, --CH2 --CH2)3CH2 --), 1.70-2.50 (4H, m, --CH2 --CH2)3CH2 --), 2.85-3.66 (4H, m, C5 --H), 4.69 (1H, dd, J=8.2, 6.0 Hz, C4 --H), 5.13 (1H, m, C4 --H), 6.16 (1H, s, C2 --H), 6.43 (1H, s, C2 -- H), 7.3-8.3 (8H, m, arom. H). TLC: Rf value* 0.33. cooling filtered to give the precipitates The separated crystals were collected by filtration

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

Procedure: To a stirred solution of (4R)-2-(3-nitrophenyl-4-thiazolidinecarboxylic acid (5.1 g) in 1M sodium carbonate (40 ml), heptanedioyl dichloride (2.1 g) was added dropwise under ice-cooling. The reaction mixture was stirred for 1 hour at the same temperature, and the separated crystals were filtered to give 4.7 g (69%) of the titled compound as disodium salt: mp 111°-113° C. (dec.) (water); [α]D25 +88.2° (c=0.5, methanol). IR (nujol, cm-1): 1635 (CON), 1585 (COO-), 1520 and 1355 (NO2), 1095, 730. TLC: Rf value* 0.28. cooling the separated crystals were filtered

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

Procedure: To a stirred solution of (4R)-2-(3-cyanophenyl)-4-thiazolidinecarboxylic acid (4.7 g) in 1M sodium carbonate (30 ml), heptanedioyl dichloride (2.1 g) was added dropwise under ice-cooling. The reaction mixture was stirred for 30 minutes at the same temperature, and filtered to give the precipitates. The precipitates were dissolved in hot water (100 ml), and acidified with concentrated hydrochloric acid. The separated crystals were collected by filtration to give 3.5 g (59%) of the titled compound: mp 105°-112° C.; [α]D25 +115.0° (c=1.0, methanol). IR (nujol, cm-1): 2270 (CN), 1735 (COOH), 1640 (CON), 1610 (aromatic), 1195, 790 (aromatic). NMR (DMSO-d6) δ: 0.69-1.66 (6H, m, --CH2 --CH2)3CH2 --), 1.70-2.50 (4H, m, --CH2 --CH2)3CH2 --), 2.85-3.66 (4H, m, C5 --H), 4.69 (1H, dd, J=8.2, 6.0 Hz, C4 --H), 5.13 (1H, m, C4 --H), 6.16 (1H, s, C2 --H), 6.43 (1H, s, C2 -- H), 7.3-8.3 (8H, m, arom. H). TLC: Rf value* 0.33. cooling filtered to give the precipitates The separated crystals were collected by filtration