Ethanol → HCID 178466820, compound

HRID 516464Notes

Reaction equation

HRID 516464 reaction equation
C([O:3][C:4](=[O:34])[C@H:5]([OH:33])[CH2:6][C@H:7]([NH:22][C:23]([C:25]1[CH:29]=[C:28]([C:30](=[O:32])[CH3:31])[NH:27][N:26]=1)=[O:24])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[CH:11][CH:10]=1)C.[Li+].[OH-].O.CCO>>[C:30]([C:28]1[NH:27][N:26]=[C:25]([C:23]([NH:22][C@H:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=3)=[CH:13][CH:14]=2)[CH2:6][C@@H:5]([OH:33])[C:4]([OH:34])=[O:3])=[O:24])[CH:29]=1)(=[O:32])[CH3:31]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 178472576HCID 178472576, compound

Product 1

HCID 178466820HCID 178466820, compoundYield 16.8%

Procedure

(2R,4R)-4-[(5-Acetyl-1H-pyrazole-3-carbonyl)amino]-5-(3′-chlorobiphenyl-4-yl)-2-hydroxy-pentanoic acid ethyl ester (72 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 (11.5 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-ac369a57d8154fad9d4854d17df2476f
Source dataset
uspto-grants-2015_08
Patent number
US09108934B2

Reaction notes

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