Z-Lys(Boc)-Lys(Boc)-Pro-NH2 → Z-Lys(Boc)-Lys(Boc)-Lys(Boc)-Pro-NH2

HRID 328758Notes

Reaction equation

HRID 328758 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:15]([NH:17][C@H:18]([C:31]([N:33]1[CH2:40][CH2:39][CH2:38][C@H:34]1[C:35]([NH2:37])=[O:36])=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].ON1C(=O)CCC1=O.[CH2:59]([O:66][C:67]([NH:69][C@H:70]([C:83]([OH:85])=O)[CH2:71][CH2:72][CH2:73][CH2:74][NH:75][C:76]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77])=[O:68])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>CO.[Pd]>[NH:69]([C:67]([O:66][CH2:59][C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)=[O:68])[C@H:70]([C:83]([NH:1][C@H:2]([C:15]([NH:17][C@H:18]([C:31]([N:33]1[CH2:40][CH2:39][CH2:38][C@H:34]1[C:35]([NH2:37])=[O:36])=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])=[O:85])[CH2:71][CH2:72][CH2:73][CH2:74][NH:75][C:76]([O:78][C:79]([CH3:80])([CH3:81])[CH3:82])=[O:77]

Participants

5

Reactant 2

HCID 131710716Z-Lys(Boc)-Lys(Boc)-Pro-NH2HCID 131710718Nalpha-benzyloxycarbonyl-Nepsilon-t-butyloxycarbonyl-L-lysine N-hydroxy-succinimide

Product 1

HCID 131710717Z-Lys(Boc)-Lys(Boc)-Lys(Boc)-Pro-NH2Yield 5.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
4 °C

Procedure

Compound XV (1.06 g, 1.5 mmoles) is hydrogenolyzed over palladium in methanol for 3 hours. After the solvent have been removed by evaporation in vacuo the residue is dissolved in ethyl acetate and chilled in an ice bath. To this is added Nα -benzyloxycarbonyl-Nε -t-butyloxycarbonyl-L-lysine N-hydroxy-succinimide (0.72 g, 1.5 mmoles) and the mixture is stirred at 4° C overnight. The precipitates which has separated are filtered off, washed with ice-cold ethyl acetate and dried in vacuo (1.31 g). An additional quantity of the product is obtained upon concentration of the filtrate (0.08 g). The combined precipitates are dissolved in methanol and most of the solvent is removed by evaporation in vacuo. The resulting sirupy residue is precipitated from ethyl acetate (20 ml)-ether (20 ml); yield 1.35 g (96%).

Workup

  1. customAfter the solvent have been removed by evaporation in vacuo the residue
  2. dissolutionis dissolved in ethyl acetate
  3. temperaturechilled in an ice bath
  4. customThe precipitates which
  5. customhas separated
  6. filtrationare filtered off
  7. washwashed with ice-cold ethyl acetate
  8. customdried in vacuo (1.31 g)

Sources & evidence

ORD record
ord-a5a72714fba047ccbdd9c813c97817bb
Source dataset
uspto-grants-1977_04
Patent number
US04018753

Reaction notes

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