Sodium Hydroxide → HCID 13242795, compound

HRID 1046676Notes

Reaction equation

HRID 1046676 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-634f7c5fa0b542d2a7574b26df3c1ad3
Source dataset
uspto-grants-2013_10
Patent number
US08569351B2

Reaction notes

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