Reaction SMILES: [CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@H:21]([C@@:39]([OH:51])([CH2:47][C:48]([O-])=[O:49])[C:40]([O:42]C(C)(C)C)=[O:41])/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:20])[C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[Cl-].[NH4+].[CH:54]1C=CC2N(O)N=NC=2C=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C.C(OC1C=CC(C[C@H](NC([C@@H](/C=C/CCCCCCC(=O)CCCCCCC)[C@](CC(=O)N)(O)C(OC(C)(C)C)=O)=O)C(OC)=O)=CC=1)C#CC.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>C(O)=O.C1COCC1.CN(C=O)C>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C@@:39]([OH:51])([CH2:47][CH2:48][O:49][CH3:54])[C:40]([OH:42])=[O:41])=[O:20])[C:14]([OH:16])=[O:15])=[CH:10][CH:11]=1)[C:2]#[C:3][CH3:4]
Reactant: On1nnc2ccccc21
Reactant: CC#CCOc1ccc(C[C@H](NC(=O)[C@@H](/C=C/CCCCCCC(=O)CCCCCCC)[C@@](O)(CC(=O)[O-])C(=O)OC(C)(C)C)C(=O)OC)cc1
Agent: CC#CCOc1ccc(C[C@H](NC(=O)[C@@H](/C=C/CCCCCCC(=O)CCCCCCC)[C@@](O)(CC(N)=O)C(=O)OC(C)(C)C)C(=O)OC)cc1
Agent: CCN=C=NCCCN(C)C
Agent: Cl
Solvent: CCN(C(C)C)C(C)C
Solvent: C1CCOC1
Solvent: O=C(OC(=O)C(F)(F)F)C(F)(F)F
Product: CC#CCOc1ccc(C[C@H](NC(=O)[C@@H](/C=C/CCCCCCC(=O)CCCCCCC)[C@@](O)(CCOC)C(=O)O)C(=O)O)cc1
Temperature: 25 °C
Reaction time: 24 h
Yield: 20.5 %

Procedure:
To a mixture of No. 5317776, 1-tert-butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (863 mg, 1.21 mmol), ammonium chloride (324 mg, 6.06 mmol), and DMF (40 mL) were added HOBt (735 mg, 5.44 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1,043 mg, 5.44 mmol), and N,N-diisopropylethylamine (1.57 mL, 9.11 mmol), and the mixture was stirred at room temperature for 1 day. After confirming the consumption of the starting materials by LCMS, ethyl acetate was added. The mixture was washed with water and a saturated brine, and dried over anhydrous sodium sulfate. The filtrate was then concentrated under reduced pressure. The resulting residue was purified with SP1 (SiO2 cartridge, 5% methanol/dichloromethane, Rf=0.3) to obtain No. 5463635, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-carbamoylmethyl-2-hydroxy-12-oxo-nonadec-4-enoate (672 mg, 78%, ESI (LC/MS positive mode) m/z 713 (M+H); Rt 2.97 min.). A mixture of No. 5463635 and THF (30 mL) was cooled to 0° C., and trifluoroacetic acid anhydride (145 μL, 1.04 mmol) and triethylamine (263 μL, 1.89 mmol) were added. After stirring for 3 hours, the consumption of the starting materials was confirmed by LCMS. Ethyl acetate and water were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated brine, and then dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure to obtain No. 6801972, tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-carbamoylmethyl-2-hydroxy-12-oxo-nonadec-4-enoate (600 mg, 91%, ESI (LC/MS positive mode) m/z 695 (M+H); Rt 3.28 min.). To No. 6801972 (520 mg, 0.748 mmol) was added formic acid (15 mL) and the mixture was stirred at room temperature. After confirming the consumption of the starting materials by LCMS, formic acid was distilled off under reduced pressure. The resulting residue was purified by preparative HPLC. The obtained fraction was freeze-dried to obtain the title compound (160 mg, 33% yield, white solid).