Lithium Hydroxide → HCID 11305244, compound

HRID 2220272Notes

Reaction equation

HRID 2220272 reaction equation
Cl.C[O:3][C:4](=[O:8])[CH2:5][CH2:6][NH2:7].[H-].[Na+].Br[CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[O:20][C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[C:23]([C:33]([F:36])([F:35])[F:34])[CH:22]=3)=[N:18][C:17]=2[CH:37]=1.[Li+].[OH-]>CN(C=O)C.O>[F:35][C:33]([F:34])([F:36])[C:23]1[CH:22]=[C:21]([C:19]2[O:20][C:16]3[CH:15]=[CH:14][C:13]([CH2:12][NH:7][CH2:6][CH2:5][C:4]([OH:3])=[O:8])=[CH:37][C:17]=3[N:18]=2)[CH:26]=[CH:25][C:24]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 24758Sodium hydrideHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 684533265-(Bromomethyl)-2-[2-(trifluoromethyl)[1,1'-biphenyl]-4-yl]-1,3-benzoxazole

Product 1

HCID 11305244HCID 11305244, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of β-alanine methyl ester hydrochloride salt (2 eq) in dry DMF (0.5 M) is added NaH (3.5 eq). After stirring at room temperature for 10 minutes, a solution of 5-bromomethyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzooxazole (1 eq) in dry DMF (1 M) is added. The resulting mixture is stirred at room temperature for 2 hours. It is diluted with H2O and extracted with EtOAc. The organic solution is washed with brine and dried over Na2SO4. After concentration, the residue is dissolve in MeOH (0.2 M) and treated with 2N LiOH solution (3 eq) for 10 hours. The final compound is purified by preparative LCMS to give 3-{[2-(2-trifluoromethyl-biphenyl-4-yl)-benzooxazol-5-ylmethyl]-amino}-propionic acid; 1H NMR (400 MHz, CD3OD) δ 2.74 (t, J=6.7 Hz, 2H), 3.30 (t, J=6.8 Hz, 2H), 4.39 (s, 2H), 7.34 (m, 2H), 7.43 (m, 3H), 7.57 (m, 2H), 7.78 (d, J=8.3 Hz, 1H), 7.94 (s, 1H), 8.43 (d, J =8.0 Hz, 1H), 8.59 (s, 1H). MS: (ES+): 441.3 (M+1)+.

Workup

  1. stirringThe resulting mixture is stirred at room temperature for 2 hours
  2. extractionextracted with EtOAc
  3. washThe organic solution is washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentration
  6. dissolutionthe residue is dissolve in MeOH (0.2 M)
  7. customThe final compound is purified by preparative LCMS

Sources & evidence

ORD record
ord-62e577acedb34499b55449bc74118740
Source dataset
uspto-grants-2008_08
Patent number
US07417065B2

Reaction notes

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