Water → HCID 21709352, compound

HRID 651741Notes

Reaction equation

HRID 651741 reaction equation
O.[OH-].[Na+].[C:4]([CH2:6][CH2:7][N:8]([CH2:48][CH2:49][C:50]#[N:51])[CH2:9][CH2:10][N:11]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])#[N:5].C(OC(OC(=O)C(C1C=CC=CC=1)=O)=O)(C)(C)C>[Ni].[OH-].[K+]>[NH2:5][CH2:4][CH2:6][CH2:7][N:8]([CH2:48][CH2:49][CH2:50][NH2:51])[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21709353HCID 21709353, compoundHCID 86757288HCID 86757288, compound

Product 1

HCID 21709352HCID 21709352, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 14797Potassium HydroxideSolvent

Procedure

2.5 g of Raney nickel are added to 50 ml of water. With stirring, 4.5 g of sodium hydroxide are added so rapidly thereto that the water does not quite boil over, and the whole is then stirred for half an hour. 320 mg (0.48 mmol, MW 671.2) of N′,N′-bis(2-cyanoethyl)-N,N-dioctadecylethylenediamine are taken up in 500 ml of 0.5M potassium hydroxide solution (in EtOH/water 95:5 v/v). The activated Raney nickel is separated from the supernatant by decanting and is added to the starting solution. The whole is then hydrogenated for 24 hours using a hydrogenation plant. After removing the solvent by rotary evaporation, the residue is dissolved in 5 ml of methylene chloride. 500 mg (2.02 mmol, MW 246.27) of O-(tert-butoxycarbonyl)-phenylglyoxylic acid nilrile oxime (BOC-ON) are added thereto and the whole is stirred at room temperature for 24 hours. Subsequently, concentration by rotary evaporation is carried out. The crude product is purified by flash chromatography. The product is then taken up in 10 ml of a 1:3 v/v mixture of trifluoroacetic acid and methylene chloride. After 2 to 3 hours, the whole is subject to rotary evaporation and dried for 0.5 hours under a high vacuum. Finally, lyophilisation from butanol/water (1:1 v/v) is carried out

Workup

  1. stirringis then stirred for half an hour
  2. customThe activated Raney nickel is separated from the supernatant
  3. customby decanting
  4. additionis added to the starting solution
  5. customAfter removing the solvent
  6. customby rotary evaporation
  7. dissolutionthe residue is dissolved in 5 ml of methylene chloride
  8. stirringthe whole is stirred at room temperature for 24 hours
  9. concentrationSubsequently, concentration
  10. customby rotary evaporation
  11. customThe crude product is purified by flash chromatography
  12. additionThe product is then taken up in 10 ml of a 1:3 v/v mixture of trifluoroacetic acid and methylene chloride
  13. waitAfter 2 to 3 hours
  14. customthe whole is subject to rotary evaporation
  15. customdried for 0.5 hours under a high vacuum

Sources & evidence

ORD record
ord-d22d06c03d4a4dedb080d068798b4a0e
Source dataset
uspto-grants-2001_08
Patent number
US06281371B1

Reaction notes

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