Ethanol → HCID 178466821, compound

HRID 516462Notes

Reaction equation

HRID 516462 reaction equation
C([O:3][C:4](=[O:35])[C@H:5]([OH:34])[CH2:6][C@H:7]([NH:23][C:24]([C:26]1[CH:30]=[C:29]([C:31](=[O:33])[CH3:32])[NH:28][N:27]=1)=[O:25])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[F:22])=[CH:11][CH:10]=1)C.[Li+].[OH-].O.CCO>>[C:31]([C:29]1[NH:28][N:27]=[C:26]([C:24]([NH:23][C@H:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=3[F:22])=[CH:11][CH:10]=2)[CH2:6][C@@H:5]([OH:34])[C:4]([OH:35])=[O:3])=[O:25])[CH:30]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 178472578HCID 178472578, compound

Product 1

HCID 178466821HCID 178466821, compoundYield 16.3%

Procedure

(2R,4R)-4-[(5-Acetyl-1H-pyrazole-3-carbonyl)amino]-5-(5′-chloro-2′-fluorobiphenyl-4-yl)-2-hydroxypentanoic acid ethyl ester (75 mg, 150 μmol) was stirred at room temperature with LiOH (10.8 mg, 450 μmol) in water (450 μL, 25 mmol) and EtOH (450 μL, 7.7 mmol), overnight. The solvent was removed and the remaining material was purified by preparative HPLC to yield the title compound (11.6 mg) as a TFA salt.

Workup

  1. customThe solvent was removed
  2. customthe remaining material was purified by preparative HPLC

Sources & evidence

ORD record
ord-faec6ab26afc44c18617528319cd6028
Source dataset
uspto-grants-2015_08
Patent number
US09108934B2

Reaction notes

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