Tetrahydrofuran → 2-(N-benzyl-4-nitrobenzamido)-2-phenylacetic acid

HRID 1951576Notes

Reaction equation

HRID 1951576 reaction equation
[CH2:1]([N:8]([CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21]([O:23]C)=[O:22])[C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.O.[OH-].[Li+]>CO.O>[CH2:1]([N:8]([CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:21]([OH:23])=[O:22])[C:9](=[O:19])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 57465368methyl 2-(N-benzyl-4-nitrobenzamido)-2-phenylacetate

Product 1

HCID 574653692-(N-benzyl-4-nitrobenzamido)-2-phenylacetic acidYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

to a room temperature solution of methyl 2-(N-benzyl-4-nitrobenzamido)-2-phenylacetate (7.63 g, 18.9 mmol) dissolved in 40 mL methanol and 30 mL THF was added a solution of lithium hydroxide monohydrate (1.95 g, 46.5 mmol) dissolved in 15 mL water. The solution turned dark brown and gradually turned light orange over 15 minutes. After 30 minutes the solvent was removed under reduced pressure and the concentrate was diluted with 50 mL water and extracted with 2×50 mL dichloromethane. The organic extracts were combined and washed with 50 mL brine then stirred over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a colorless foamy solid (7.30 g, 99%). ESI− m/z=779.2 [2M−H]−.

Workup

  1. customAfter 30 minutes the solvent was removed under reduced pressure
  2. additionthe concentrate was diluted with 50 mL water
  3. extractionextracted with 2×50 mL dichloromethane
  4. washwashed with 50 mL brine
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-b48381ba46a647ae86b03f431977f87b
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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