Lithium Hydroxide → (+/-)-3-Phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoic acid

HRID 989903Notes

Reaction equation

HRID 989903 reaction equation
[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[O:21])[N:19]=2)[CH2:8][C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[O:21])[N:19]=2)[CH2:8][C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11189784Ethyl (+/-)-3-phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoate

Product 1

HCID 9822714(+/-)-3-Phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoic acidYield 51.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl (±)-3-phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoate (131 mg, 0.30 mmole) in 1:1 THF/H2O (10 mL) was added 1N LiOH (0.36 mL, 0.36 mmole). After 18 hr, the mixture was concentrated under reduced pressure. The residue was dissolved in 20 mL H2O then acidified to pH 6 using 10% HCl. The resulting cloudy solution was extracted with CH2Cl2 (3×75 mL). The organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was triturated with Et2O to give the title compound as a white solid (63 mg, 51%) which was collected by filtration. MS (ES) m/e 409 (M+H)+. Anal. Calcd for C22H24N4O4.0.75 H2O, 1.5 HCl: C, 55.44; H, 5.71; N, 11.75. Found: C, 55.49; H, 5.54; N, 11.63.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 20 mL H2O
  3. extractionThe resulting cloudy solution was extracted with CH2Cl2 (3×75 mL)
  4. dry with materialThe organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-ca24fea2bb4e4459ae00c78152da7b25
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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