Hydrochloric Acid → (R)-3-[N'-(5-Acetyl-2H-pyrazole-3-carbonyl)-N-(5'-chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic Acid 2-Methoxyethyl Ester
Reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:9]([NH:11][N:12]([CH2:28][C@@H:29]([OH:33])[C:30]([OH:32])=[O:31])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=3[F:27])=[CH:16][CH:15]=2)=[O:10])[NH:7][N:8]=1)(=[O:3])[CH3:2].[CH3:34][O:35][CH2:36][CH2:37]O.Cl.O1CCOCC1>>[CH3:34][O:35][CH2:36][CH2:37][O:31][C:30](=[O:32])[C@H:29]([OH:33])[CH2:28][N:12]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=2[F:27])=[CH:16][CH:15]=1)[NH:11][C:9]([C:6]1[NH:7][N:8]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=1)=[O:10]Participants
5
Reactant 4
Product 1
Procedure
(R)-3-[N′-(5-Acetyl-2H-pyrazole-3-carbonyl)-N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic acid (10.0 mg, 21 μmol) was combined with 2-methoxyethanol (0.1 mL, 1.3 mmol). A solution of 4 M HCl in dioxane (53 μL, 0.2 mmol) was added, and the resulting mixture was stirred for 1 hour at room temperature. LC/MS showed the mass of the desired product. The mixture was concentrated by rotary evaporation and purified (reverse phase column) to yield the title compound (2.7 mg, purity 95%) as a white solid TFA salt. MS m/z [M+H]+ calc'd for C25H26ClFN4O6, 533.15. found 533.1.
Sources & evidence
- ORD record
- ord-5a464ea69ab34676baf85a4b2efa2601
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871792B2
Reaction notes
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