Triethylamine → HCID 11687141, compound

HRID 851731Notes

Reaction equation

HRID 851731 reaction equation
[NH2:1][C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH2:12])=[O:11])=[O:7])[CH2:3][CH2:4][CH3:5].Cl.C(N(CC)CC)C>CN(C=O)C>[NH2:1][C@H:2]([C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([NH2:12])=[O:11])=[O:7])[CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 8471Triethylamine2×HCID 70564477HCID 70564477, compound

Product 1

HCID 11687141HCID 11687141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.38 g (9.5 mmoles) of H-Nva-Pro-NH2.HCl are suspended in 30 ml of DMFA, and 3.09 g (10 mmoles) of Kpc-OPFP and 1.33 ml (9.5 mmoles) of triethylamine are added to the stirred suspension under ice cooling. After 5 minutes of stirring further 1.33 ml (9.5 mmoles) of triethylamine are added, the mixture is stirred for additional 20 minutes, and then evaporated in vacuo. The crystalline residue is triturated with ether, filtered, and washed with cold alcohol on the filter. The resulting 3.66 g of crude product are dissolved in water, the solution is decolourized, filtered, the clear filtrate is evaporated, and the crystalline residue is triturated with 10 ml of alcohol. The mixture is allowed to stand at a cool place, and then the substance is filtered off. 2.10 g (65%) of Kpc-Nva-Pro-NH2 are obtained; m.p.: 192°-193° C., Rf5 =0.31, [α]D25 =-83.2° (c=1%, in acetic acid).

Workup

  1. additionare added
  2. customevaporated in vacuo
  3. customThe crystalline residue is triturated with ether
  4. filtrationfiltered
  5. washwashed with cold alcohol on the filter
  6. dissolutionThe resulting 3.66 g of crude product are dissolved in water
  7. filtrationfiltered
  8. customthe clear filtrate is evaporated
  9. customthe crystalline residue is triturated with 10 ml of alcohol
  10. filtrationthe substance is filtered off

Sources & evidence

ORD record
ord-ac7b66ba21ad4868a1841167aeaa2838
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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