Sodium Hydroxide → HCID 13242795, compound

HRID 919330Notes

Reaction equation

HRID 919330 reaction equation
C([O:3][C:4](=[O:24])[CH:5]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:6]([NH:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])C.[OH-].[Na+]>C1COCC1.CO.O>[CH2:17]([CH:5]([C:6]([NH:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])[C:4]([OH:24])=[O:3])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 57483942HCID 57483942, compound

Product 1

HCID 13242795HCID 13242795, compoundYield 81.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 2-benzyl-N-benzyloxy-malonamic acid ethyl ester (19 g, 58.1 mmol) dissolved in a mixture of THF (70 mL) and MeOH (200 mL) was added a solution of NaOH (5.4 g, 135 mmol) in water (100 mL). The mixture was stirred at room temperature for 24 hours, and evaporated to remove volatile organic solvents. The aqueous residue was diluted with water (200 mL), and washed with DCM (200 mL). The aqueous layer was saved and acidified to pH˜4 by adding concentrated HCl. The desired product was precipitated, washed with water, dissolved in acetone (200 mL), and evaporated to dryness, affording intermediate (12a) as a white solid (14.2 g). 1H-NMR (CD3OD, 300 MHz) δ (ppm) 7.20-7.06 (m, 5H), 4.60-4.56 (d, 1H), 4.42-4.38 (d, 1H), 3.10-2.98 (m, 2H).

Workup

  1. customevaporated
  2. customto remove volatile organic solvents
  3. additionThe aqueous residue was diluted with water (200 mL)
  4. washwashed with DCM (200 mL)
  5. additionby adding concentrated HCl
  6. customThe desired product was precipitated
  7. washwashed with water
  8. dissolutiondissolved in acetone (200 mL)
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-8a0502edc5f540febe7b5555b3f550cb
Source dataset
uspto-grants-2016_03
Patent number
US09273008B2

Reaction notes

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