Lithium Hydroxide → HCID 71657612, compound

HRID 1428677Notes

Reaction equation

HRID 1428677 reaction equation
C([O:3][C:4](=[O:35])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:19]=[C:14]2[CH:13]=[C:12]1[CH:32]1[CH2:34][CH2:33]1)C.[Li+].[OH-]>C1COCC1.O>[CH:32]1([C:12]2[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:35])=[O:3])[C:15]3=[N:16][C:17]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:19]=[C:14]3[CH:13]=2)[CH2:33][CH2:34]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86690326HCID 86690326, compound

Product 1

HCID 71657612HCID 71657612, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

7-(6-Cyclopropyl-2,3-diphenyl-pyrrolo[2,3-b]pyrazin-5-yl)-heptanoic acid ethyl ester (step 1) (250 mg, 0.535 mmol) in THF (6 ml) and water (2 ml) was treated with LiOH.monohydrate (45 mg, 1.069 mmol) and stirred at room temperature for 12 hours followed by heating at 60° C. for 10 hours. The mixture was concentrated under reduced pressure. The residue was dissolved in water and washed with diethyl ether (×1). The aqueous was acidified using citric acid, and extracted with EtOAc. The organic solvent was dried (Na2SO4) and the solvent was removed under reduced pressure. Purification of the product by chromatography on silica eluting with 1% MeOH in DCM, followed by further purification using preparative HPLC according to the following conditions to afforded the titled compound;

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. washwashed with diethyl ether (×1)
  4. extractionextracted with EtOAc
  5. dry with materialThe organic solvent was dried (Na2SO4)
  6. customthe solvent was removed under reduced pressure
  7. customPurification of the product by chromatography on silica eluting with 1% MeOH in DCM
  8. customfollowed by further purification

Sources & evidence

ORD record
ord-cf524ab1ecbb4395aff04495c097dbe0
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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