Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:47]=[CH:48][C:49]=1[Cl:50])[CH2:8][O:9][CH:10]1[O:15][CH:14]([CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=2)[CH:13]([O:26][CH:27]2[O:36][CH:35]3[CH:30]([O:31][CH:32]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[O:33][CH2:34]3)[CH:29]([OH:43])[CH:28]2[OH:44])[CH:12]([OH:45])[CH:11]1[OH:46])(=[O:3])[CH3:2].[K+].[Br-]>O>[C:14]([O:45][CH:12]1[CH:11]([O:46][C:18](=[O:17])[CH3:19])[CH:10]([O:9][CH2:8][C:7]2[CH:47]=[CH:48][C:49]([Cl:50])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[O:15][CH:14]([CH2:16][O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=2)[CH:13]1[O:26][CH:27]1[O:36][CH:35]2[CH:30]([O:31][CH:32]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[O:33][CH2:34]2)[CH:29]([O:43][C:8](=[O:9])[CH3:7])[CH:28]1[O:44][C:1](=[O:3])[CH3:2])(=[O:15])[CH3:13]
Reactant: CC(=O)Nc1cc(COC2OC(COC(=O)c3cccnc3)C(OC3OC4COC(c5ccccc5)OC4C(O)C3O)C(O)C2O)ccc1Cl
Agent: [Br-]
Agent: [K+]
Solvent: O
Product: CC(=O)Nc1cc(COC2OC(COC(=O)c3cccnc3)C(OC3OC4COC(c5ccccc5)OC4C(OC(C)=O)C3OC(C)=O)C(OC(C)=O)C2OC(C)=O)ccc1Cl

Procedure:
The title compound was prepared as a white foam (0.157 g, 73%) from nicotinic acid 6-(3-acetylamino-4-chloro-benzyloxy)-3-(7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester using a procedure similar to Example 25, mp >112° C. (decomp.); 1H NMR (DMSO-d6) δ1.94 (s, 3H), 1.95 (s, 3H), 1.98 (s, 3H), 1.99 (s, 3H), 2.05 (s, 3H), 3.64 (t, J=9.4 Hz, 1H), 3.69-3.76 (m, 1H), 3.79 (dd, J=4.2, 9.2 Hz, 1H), 3.87 (t, J=9.4 Hz, 1H), 4.13-4.19 (m, 1H), 4.26 (t, J=9.4 Hz, 1H), 4.48 (dd, J=4.0, 12.3 Hz, 1H), 4.64 (ABq, J=12.7 Hz, Δδ=0.14, 2H), 4.71-4.76 (m, 1H), 4.82 (dd, J=8.1, 9.2 Hz, 1H), 4.87-4.92 (m, 2H), 5.26 (t, J=10.1 Hz, 1H), 5.32-5.38 (m, 2H), 5.5 (s, 1H), 7.04 (dd, J=1.8, 8.1 Hz, 1H), 7.29-7.36 (m, 5H), 7.42 (d, J=8.1 Hz, 1H), 7.58 (dd, J=4.8, 8.1 Hz, 1H), 7.61 (s, 1H), 8.39 (dt, J=2.0, 7.9 Hz, 1H), 8.84 (dd, J=1.5, 4.6 Hz, 1H), 9.17-9.19 (m, 1H), 9.49 (s, 1H); IR (KBr) 3410, 2940, 2860, 1755, 1690, 1600, 1530, 1450, 1420, 1380, 1290, 1240, 1140, 1055, 1030, and 995 cm−1; mass spectrum [(+) FAB], m/z 885 (M+H)+, 907 (M+Na)+; Anal. Calcd. for C42H45ClN2O17.1.0 H2O: C, 55.85; H, 5.24; N, 3.10, Found: C, 55.61; H, 4.89; N, 2.99.
Reaction SMILES: [C:1]([OH:6])(=[O:5])[CH:2]([CH3:4])[OH:3].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4:23].[OH-].[Na+:25].C(O)CO>O>[Na+:25].[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[Ti+4:23].[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[OH:3].[C:1]([O-:6])(=[O:5])[CH:2]([CH3:4])[OH:3]
Reactant: CC(O)C(=O)O
Agent: [Ti+4]
Agent: CC(C)[O-]
Agent: [Na+]
Solvent: OCCO
Solvent: O
Product: CC(O)C(=O)[O-]
Temperature: 70 °C
Reaction time: 1 h

Procedure:
Lactic acid (226.8 g, 2.52 mol) was dissolved in hot water (371 g) in a flask of 3 L having an agitator, a condenser and a thermometer. Titanium tetraisopropoxide (285 g, 1.00 mol) was slowly added to this solution being agitated, from a drop funnel. This mixture was heated and circulated for one hour to prepare a cloud solution, and by this, isopropanol/water mixture was distilled under a pressure-reduced condition. The product was cooled down to a temperature lower than 70° C., and then, aqueous solution containing NaOH (380 g, 3.04 mol) at 32% by weight was slowly added to this solution being agitated, from a drop funnel. The obtained product was filtered, then mixed with ethylene glycol (504 g, 8 mol), thereafter heated under a pressure-reduced condition to remove isopropanol/water, and a slightly cloud light yellow product (Ti content: 5.6% by weight) was obtained (titanium lactate sodium chelate compound).