Succinic anhydride → HCID 67864256, compound

HRID 476696Notes

Reaction equation

HRID 476696 reaction equation
C(O)(=O)C.[CH3:5][O:6][P:7]([CH2:27][NH2:28])([CH2:9][CH:10]([C:15](=[O:26])[NH:16][C@H:17]([C:22](=[O:25])[NH:23][CH3:24])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8].[C:29]1(=O)[O:34][C:32](=[O:33])[CH2:31][CH2:30]1.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.C(N(CC)CC)C>[CH3:5][O:6][P:7]([CH2:9][CH:10]([C:15](=[O:26])[NH:16][C@H:17]([C:22](=[O:25])[NH:23][CH3:24])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:11][CH:12]([CH3:14])[CH3:13])([CH2:27][N:28]1[C:32](=[O:33])[CH2:31][CH2:30][C:29]1=[O:34])=[O:8]

Participants

7

Reactant 4

HCID 7922Succinic anhydrideHCID 10868DicyclohexylcarbodiimideHCID 86743557(aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid methyl ester acetateHCID 178418300HCID 178418300, compound

Product 1

HCID 67864256HCID 67864256, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

0.36 g of (aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid methyl ester acetate, prepared as described in Example 2(A)(i), was dissolved in 10 ml of dichloromethane and 0.17 g of succinic anhydride and 0.17 g of triethylamine were added. After stirring at room temperature for 2 hours, 0.2 g of hydroxybenzotriazole and 0.2 g of N,N'-dicyclohexylcarbodiimide were added. The mixture was stirred at room temperature for 18 hours and then filtered in order to remove dicyclohexylurea. The filtrate was washed twice with 15 ml of saturated sodium hydrogen carbonate solution each time. After drying over anhydrous sodium sulfate the solvent was removed by evaporation to give a colorless gum. This gum was purified by flash chromatography on silica gel using ethyl acetate/methanol (8:1) for the elution. There was obtained 0.23 g of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl](succinimidomethyl)phosphinic acid methyl ester in the form of a white foam.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. filtrationfiltered in order
  3. customto remove dicyclohexylurea
  4. washThe filtrate was washed twice with 15 ml of saturated sodium hydrogen carbonate solution each time
  5. dry with materialAfter drying over anhydrous sodium sulfate the solvent
  6. customwas removed by evaporation
  7. customto give a colorless gum
  8. customThis gum was purified by flash chromatography on silica gel
  9. washfor the elution

Sources & evidence

ORD record
ord-609c303e8a564622bc53096aa20e0949
Source dataset
uspto-grants-1989_12
Patent number
US04885283

Reaction notes

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