Acetyl chloride → HCID 86705121, compound

HRID 541548Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[C:5]([C:8]1[CH:9]=[C:10]([C:13]([NH:15][N:16]([CH2:32][C@@H:33]([OH:37])[C:34]([OH:36])=[O:35])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=3[F:31])=[CH:20][CH:19]=2)=[O:14])[NH:11][N:12]=1)(=[O:7])[CH3:6].C1COCC1>>[C:1]([O:37][C@H:33]([CH2:32][N:16]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=2[F:31])=[CH:20][CH:19]=1)[NH:15][C:13]([C:10]1[NH:11][N:12]=[C:8]([C:5](=[O:7])[CH3:6])[CH:9]=1)=[O:14])[C:34]([OH:36])=[O:35])(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 6367Acetyl chloride

HCID 8028Tetrahydrofuran

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 86705121HCID 86705121, compoundYield 56.1%

Procedure

Acetyl chloride (30 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 (12.2 mg) as a TFA salt. MS m/z [M+H]+ calc'd for C24H22ClFN4O6, 517.12. found 517.2.

Workup

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

Sources & evidence

ORD record: ord-891b5affcd4e45dba0f4b6e3e005e62f
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871792B2

Reaction notes

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