Tetrahydrofuran → HCID 86705120, compound

HRID 541547Notes

Reaction equation

[C:1](Cl)(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[C:8]([C:11]1[CH:12]=[C:13]([C:16]([NH:18][N:19]([CH2:35][C@@H:36]([OH:40])[C:37]([OH:39])=[O:38])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=3[F:34])=[CH:23][CH:22]=2)=[O:17])[NH:14][N:15]=1)(=[O:10])[CH3:9].C1COCC1>>[C:8]([C:11]1[CH:12]=[C:13]([C:16]([NH:18][N:19]([CH2:35][C@@H:36]([O:40][C:1](=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4])[C:37]([OH:39])=[O:38])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=3[F:34])=[CH:23][CH:22]=2)=[O:17])[NH:14][N:15]=1)(=[O:10])[CH3:9]

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 66054Isovaleryl chloride

HCID 86705116(R)-3-[N'-(5-Acetyl-2H-pyrazole-3-carbonyl)-N-(5'-chloro-2'-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic acid

Product 1

HCID 86705120HCID 86705120, compoundYield 50.1%

Procedure

Isovaleryl chloride (51.4 μL, 421.2 μmol) and (R)-3-[N′-(5-acetyl-2H-pyrazole-3-carbonyl)-N-(5′-chloro-2′-fluorobiphenyl-4-ylmethyl)hydrazino]-2-hydroxypropionic acid (20.0 mg, 42.1 μmol) were combined in THF (205 μL, 2.5 mmol), and stirred overnight at room temperature. The solvent was evaporated and the residue was purified (reverse phase HPLC column) to yield the title compound (11.8 mg) as a TFA salt. MS m/z [M+H]+ calc'd for C27H28ClFN4O6, 559.17. found 559.1.

Workup

customThe solvent was evaporated
customthe residue was purified (reverse phase HPLC column)

Sources & evidence

ORD record: ord-992d504909e9414f86db29e26f33262d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871792B2

Reaction notes

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