Lithium Hydroxide → HCID 21091661, compound

HRID 1348807Notes

Reaction equation

HRID 1348807 reaction equation
[ClH:1].C[O:3][C:4](=[O:18])[CH:5]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)[CH2:6][CH2:7][NH2:8].CCN([CH:25]([CH3:27])[CH3:26])C(C)C.[C:28]([N:35]1[CH:39]=[CH:38][N:37]=[CH:36]1)([N:30]1[CH:34]=[CH:33]N=C1)=[O:29].[Li+].[OH-:41]>C(Cl)Cl>[CH2:10]([N:9]1[C:5](=[O:41])[C:6]2[C:36](=[CH:4][C:5]([Cl:1])=[CH:6][CH:7]=2)[N:37]=[C:38]1[CH:39]1[CH2:33][CH2:34][NH:30][C:28](=[O:29])[N:35]1[CH2:16][C:11]1[CH:10]=[CH:27][C:25]([CH3:26])=[CH:13][CH:12]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1.[CH3:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:9]2[CH:5]([C:4]([OH:3])=[O:18])[CH2:6][CH2:7][NH:8][C:28]2=[O:29])=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 69227997HCID 69227997, compound

Product 2

HCID 10254245HCID 10254245, compoundHCID 21091661HCID 21091661, compoundYield 200.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-2-(4-methyl-benzylamino)-butyric acid methyl ester HCl salt (923 mg, 3.13 mmol) and DIEA (1.08 mL, 6.26 mmol) in 100 mL of DCM was added carbonyldiimidazole (760 mg, 4.69 mmol). The reaction mixture was stirred for 1 hour, after which the solvents were evaporated. The residue was dissolved in 20 mL of MeOH:H2O (2:1) solution to which was added LiOH (150 mg, 6.26 mmol). The mixture was stirred at room temperature for 3 hours and then adjusted to pH ˜7 by adding Dowex-H+ resin. The solution was filtered, the solvent was evaporated, and the residue dried under vacuum to give the desired compound of Formula 304, 3-(4-methyl-benzyl)-2-oxo-hexahydro-pyrimidine-4-carboxylic acid (520 mg, 67%), which was taken on without further purification.

Workup

  1. customafter which the solvents were evaporated
  2. dissolutionThe residue was dissolved in 20 mL of MeOH:H2O (2:1) solution to which
  3. stirringThe mixture was stirred at room temperature for 3 hours
  4. filtrationThe solution was filtered
  5. customthe solvent was evaporated
  6. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-27d2749f39a1492cbcd0fde9f55b235d
Source dataset
uspto-grants-2007_05
Patent number
US07211580B2

Reaction notes

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