Ammonium Hydroxide → HCID 70561546, compound

HRID 436043Notes

Reaction equation

HRID 436043 reaction equation
[NH2:1][C@H:2]([C:4]([NH:6][CH2:7][C:8]([N:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:11])=[O:9])=[O:5])[CH3:3].[N+:26]([O-])([O-:28])=[O:27].[K+].[OH-].[NH4+]>S(=O)(=O)(O)O>[NH2:1][C@H:2]([C:4]([NH:6][CH2:7][C:8]([N:10]([C:12]1[CH:17]=[CH:16][C:15]([N+:26]([O-:28])=[O:27])=[CH:14][C:13]=1[C:18](=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:11])=[O:9])=[O:5])[CH3:3]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 70562634HCID 70562634, compound

Product 1

HCID 70561546HCID 70561546, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-5 °C

Procedure

3 g of L-alanyl-N-(2-benzoylphenyl)-N-methylglycinamide were dissolved in 10 ml of anhydrous sulphuric acid at room temperature. The resulting mixture was cooled to -5° C and treated dropwise by the addition of a solution of 0.94 g of potassium nitrate in 3 ml of anhydrous sulphuric acid. The resulting mixture was stirred at 0° C for 10 hours and finally allowed to warm to room temperature overnight. The mixture was then poured into an excess of ice-water. The pH of the mixture was adjusted to approximately pH 9 by the addition of concentrated ammonium hydroxide, care being taken to maintain the temperature at ca 0° C. The mixture obtained was extracted with several portions of dichloromethane. The combined organic phases were washed successively with 2-N sodium carbonate solution and water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue (ca 3 g) was dissolved in a minimum amount of chloroform and subjected to column chromatography on Florisil using mixtures of methanol in chloroform in increasing proportions. Fractions were collected using 5% (vol/vol) methanol in chloroform and evaporated in vacuo to give 1.75 g (52%) of pure L-alanyl-N-(2-benzoyl-4-nitrophenyl)-N-methylglycinamide as an almost colourless light-sensitive foam; [α]D20 = +2.1° (c = 1 in ethanol).

Workup

  1. temperatureto warm to room temperature overnight
  2. temperatureto maintain the temperature at ca 0° C
  3. customThe mixture obtained
  4. extractionwas extracted with several portions of dichloromethane
  5. washThe combined organic phases were washed successively with 2-N sodium carbonate solution and water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. dissolutionThe residue (ca 3 g) was dissolved in a minimum amount of chloroform
  9. temperaturein increasing proportions
  10. customFractions were collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-4f9428a4e2d04cd097e337be78114eed
Source dataset
uspto-grants-1977_02
Patent number
US04007219

Reaction notes

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