Ammonia → HCID 53902585, compound

HRID 495868Notes

Reaction equation

HRID 495868 reaction equation
Cl.[CH2:2]([N:9]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N.[CH:29]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[C:31](O)[CH:30]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.C(Cl)(Cl)Cl>[N+:35]([C:34]1[CH:29]=[CH:30][C:31]([O:19][C:18](=[O:20])[C@H:10]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:9]([CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:32][CH:33]=1)([O-:37])=[O:36]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 69745698HCID 69745698, compound

Product 1

HCID 53902585HCID 53902585, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N-dibenzyl-L-phenylalanine hydrochloride (7.64 g, 20.0 mmol) was added to 50 ml of chloroform, and 20.0 ml of 10% aqueous ammonia were added dropwise to the suspension for neutralization. The organic layer was separated, washed with 20 ml of water, then dried over magnesium sulfate, and filtered. The filtrate was concentrated, the resulting residue was dissolved in 50 ml of chloroform, and 2.89 g (20.4 mmol) of p-nitrophenol and 4.13 g (20.0 mmol) of N,N′-dicyclohexylcarbodiimide were added to the solution in this order while being cooled with ice. The mixture was reacted overnight. To the reaction solution were added 30 ml of ethyl acetate, and the N,N′-dicyclohexylurea which precipitated was removed by filtration. The filtrate was washed with a 10% potassium carbonate aqueous solution. The organic layer was separated, and concentrated. The resulting residue was redissolved in 30 ml of ethyl acetate, and the insoluble materials which precipitated were removed by filtration. The filtrate was concentrated, and the resulting crude product was purified through silica-gel column chromatography to obtain 7.77 g (16.65 mmol) of the above-mentioned compound (Ib).

Workup

  1. additionwere added dropwise to the suspension for neutralization
  2. customThe organic layer was separated
  3. washwashed with 20 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. dissolutionthe resulting residue was dissolved in 50 ml of chloroform
  8. temperaturewhile being cooled with ice
  9. customThe mixture was reacted overnight
  10. customthe N,N′-dicyclohexylurea which precipitated
  11. customwas removed by filtration
  12. washThe filtrate was washed with a 10% potassium carbonate aqueous solution
  13. customThe organic layer was separated
  14. concentrationconcentrated
  15. dissolutionThe resulting residue was redissolved in 30 ml of ethyl acetate
  16. customthe insoluble materials which precipitated
  17. customwere removed by filtration
  18. concentrationThe filtrate was concentrated
  19. customthe resulting crude product was purified through silica-gel column chromatography

Sources & evidence

ORD record
ord-6e5b36bee8ce4febb5e11fbea14e90c0
Source dataset
uspto-grants-2005_09
Patent number
USRE038796E1

Reaction notes

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