Hydrochloric Acid → (R)-3-[N'-(5-Acetyl-2H-pyrazole-3-carbonyl)-N-(5'-chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic Acid Isobutyl Ester

HRID 541540Notes

Reaction equation

HRID 541540 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].[CH2:34](O)[CH:35]([CH3:37])[CH3:36].Cl.O1CCOCC1>>[CH2:34]([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])[CH:35]([CH3:37])[CH3:36]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6560IsobutanolHCID 312751,4-DioxaneHCID 86705116(R)-3-[N'-(5-Acetyl-2H-pyrazole-3-carbonyl)-N-(5'-chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic acid

Product 1

HCID 86705117(R)-3-[N'-(5-Acetyl-2H-pyrazole-3-carbonyl)-N-(5'-chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic Acid Isobutyl EsterYield 111.8%

Procedure

(R)-3-[N′-(5-Acetyl-2H-pyrazole-3-carbonyl)-N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic acid (15.0 mg, 32 μmol) was combined with isobutyl alcohol (876 μL, 9.5 mmol). A solution of 4 M HCl in dioxane (282 μL, 1.1 mmol) was added, and the resulting mixture was stirred for 15 minutes at room temperature. The mixture was concentrated by rotary evaporation and the product lyophilized to yield the title compound (19 mg, purity 99%) as a white powder TFA salt. MS m/z [M+H]+ calc'd for C26H28ClFN4O5, 531.17. found 531.1.

Workup

  1. concentrationThe mixture was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-f514f4dc1e73425691991e11412ba1c4
Source dataset
uspto-grants-2014_10
Patent number
US08871792B2

Reaction notes

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