Lithium hydroxide, monohydrate → HCID 15549732, compound

HRID 430480Notes

Reaction equation

HRID 430480 reaction equation
[CH2:1]([CH:5]([C:11](=[O:29])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19](=[O:28])[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=2[OH:27])[CH:13]=1)C(OCC)=O)[CH2:2][CH2:3][CH3:4].O[Li].O>C1COCC1.O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:19]([NH:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11](=[O:29])[CH2:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:13]=2)=[O:28])=[C:21]([OH:27])[CH:22]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 9823290HCID 9823290, compound

Product 1

HCID 15549732HCID 15549732, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl α-butyl-3-[(4-chloro-2-hydroxybenzoyl)amino]-β-oxobenzenepropanoate (32.0 mg, 77.0 μmol) and LiOH.H2O (11.0 mg, 0.26 mmol) in THF (3.0 mL) and water (1.5 mL) was heated to 55° for 48 h. The mixture was partitioned between water and EtOAc. The aqueous layer was acidified with aqueous 10% citric acid then extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by reversed phase HPLC (Whatman Partisil® ODS-3 C18 10μ, 22×500 mm; 0 to 80% MeCN+0.06% TFA/water+0.06% TFA) to give the title compound (16.0 mg, 60% yield) as a white solid: mp 134-136°; identical to the product of example 2.

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. extractionthen extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by reversed phase HPLC (Whatman Partisil® ODS-3 C18 10μ, 22×500 mm; 0 to 80% MeCN+0.06% TFA/water+0.06% TFA)

Sources & evidence

ORD record
ord-aef35750a710442f9981b86e01f4ae74
Source dataset
uspto-grants-2001_11
Patent number
US06323202B1

Reaction notes

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