Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: C(N(C(C)C)CC)(C)C.[CH2:10]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[N+:26]([C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=1)([O-:28])=[O:27]>C(Cl)Cl>[CH2:10]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([S:35]([C:32]2[CH:33]=[CH:34][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][C:31]=2[C:39]([F:40])([F:41])[F:42])(=[O:37])=[O:36])[CH2:22][CH2:21]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
Reactant: O=[N+]([O-])c1ccc(S(=O)(=O)Cl)c(C(F)(F)F)c1
Reactant: O=C(OCc1ccccc1)N1CCNCC1
Solvent: CCN(C(C)C)C(C)C
Solvent: ClCCl
Product: O=C(OCc1ccccc1)N1CCN(S(=O)(=O)c2ccc([N+](=O)[O-])cc2C(F)(F)F)CC1
Temperature: 25 °C
Reaction time: 1 h
Yield: 86.3 %

Procedure:
Diisopropylethylamine (1.2 ml, 7.0 mmol) was added in one portion to a stirred solution of piperazine-1-carboxylic acid benzyl ester (0.76 g, 3.5 mmol) in DCM (15 ml) at room temperature. To this mixture was added 4-nitro-2-trifluoromethyl-benzenesulfonyl chloride (1.0 g, 3.5 mmol) in one portion and the mixture was stirred at room temperature under a nitrogen atmosphere for 1 hour. After this time, the mixture was diluted with DCM (20 ml), washed with HCl (1M, 20 ml) and NaOH (1M, 20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated under vacuum to give the title compound (1.43 g, 87% yield) as a purple solid. δH (500 MHz, DMSO) 8.65-8.60 (2H, m), 8.31 (1H, d), 7.38-7.29 (5H, m), 5.07 (2H, s), 3.56-3.46 (4H, m), 3.30-3.25 (4H, m). Tr=2.25 min m/z (ES+) (M+Na+) 496.
Reaction SMILES: [CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])[CH:4]=[C:3]1[C:22]([O:24]CC)=[O:23].[OH-].[Li+]>C1COCC1.O>[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]([F:20])([F:21])[F:19])=[CH:15][CH:16]=2)=[O:9])[CH:4]=[C:3]1[C:22]([OH:24])=[O:23]
Reactant: CCOC(=O)c1cc(NC(=O)Nc2ccc(OC(F)(F)F)cc2)cn1C
Agent: [Li+]
Agent: [OH-]
Solvent: O
Solvent: C1CCOC1
Product: Cn1cc(NC(=O)Nc2ccc(OC(F)(F)F)cc2)cc1C(=O)O

Procedure:
470 mg (1.27 mmol) of ethyl 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-pyrrole-2-carboxylate are initially charged in 5 ml of THF, 152 mg (6.33 mmol) of lithium hydroxide in 1 ml of water are added and the mixture is stirred under reflux overnight. The reaction mixture is concentrated, the residue is acidified with 2M hydrochloric acid and the precipitate formed is filtered off with suction and dried under reduced pressure. This gives a solid.
Reaction SMILES: CC1C=C(C=C(C)C=1)C([N:7](C)[C@:8](C)([C:21]([OH:23])=O)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)=[CH:12][CH:11]=1)=O.Cl.[CH3:31][O:32][C:33](=[O:46])[C@H:34]([CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)[NH2:35].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC>CN(C=O)C.C(OCC)(=O)C>[CH3:31][O:32][C:33](=[O:46])[C@H:34]([CH2:36][C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[NH:39][CH:38]=1)[NH:35][C:21](=[O:23])[C@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)=[CH:14][CH:15]=1)[NH2:7]
Reactant: COC(=O)[C@@H](N)Cc1c[nH]c2ccccc12
Reactant: Cc1cc(C)cc(C(=O)N(C)[C@@](C)(Cc2ccc(-c3ccsc3)cc2)C(=O)O)c1
Agent: CCN=C=NCCCN(C)C
Agent: Cl
Agent: On1nnc2ccccc21
Solvent: CCOC(C)=O
Solvent: CN(C)C=O
Product: COC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H](N)Cc1ccc(-c2ccsc2)cc1
Temperature: 0 °C
Reaction time: 2 h
Yield: 54.2 %

Procedure:
To a solution of N-(3,5-dimethylbenzoyl)-N-methyl-2-methyl-3-[4-(3-thienyl)phenyl]alanine (135 mg, 0.33 mmol) in DMF are successively added tryptophan methyl ester hydrochloride (110 ml, 0.43 mmol), 1-Hydroxybenzotriazole (58 mg, 0.43 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (5.46M solution) 79μ, 0.43 mmol) at 0° C. under nitrogen atomosphere. The reaction mixture is allowed to stir at 0° C. for 2 h, then at room temperature overnight. The mixture is diluted with ethyl acetate and washed with 10% citric acid twice. The organic layer is dried over magnesium sulfate and concentrated in vacuo. The residue is chromatographed on silica with hexane/ethyl acetate (1:1) to give (D,L)-isomer (55 mg) and (L,L)-isomer (80 mg: including 15% of (D,L)-isomer) (total 67%) of 3-[4-(3-thienyl)phenyl]alanyl-tryptophan methyl ester. Hydrolysis of (D,L)-isomer (55 mg, 0.09 mmol) with lithium hydroxide hydrate (6 mg, 0.14 mmol) affords N-(3,5-Dimethylbenzoyl)-N-methyl-(D)-2-methyl-3-[4-(3-thienyl)phenyl)-alanyl-(L)-tryptophan FAB-MS m/e 592 (M-H)+.