p-Toluenesulfonic acid → Z-D-Lys(Boc)-Phe-D-Lys(Boc)-Phe-Gly-OMe

HRID 2309823Notes

Reaction equation

HRID 2309823 reaction equation
C1C=C2C(N(O)N=NC2=CC=1)=O.C1CCC(N=C=NC2CCCCC2)CC1.[NH:28]([C:56]([O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)=[O:57])[C@@H:29]([C:42]([NH:44][C@H:45]([C:53]([OH:55])=O)[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].[NH2:66][C@@H:67]([C:80]([NH:82][C@H:83]([C:91]([NH:93][CH2:94][C:95]([O:97][CH3:98])=[O:96])=[O:92])[CH2:84][C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)=[O:81])[CH2:68][CH2:69][CH2:70][CH2:71][NH:72][C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74].S(O)(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[NH:28]([C:56]([O:58][CH2:59][C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)=[O:57])[C@@H:29]([C:42]([NH:44][C@H:45]([C:53]([NH:66][C@@H:67]([C:80]([NH:82][C@H:83]([C:91]([NH:93][CH2:94][C:95]([O:97][CH3:98])=[O:96])=[O:92])[CH2:84][C:85]1[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=1)=[O:81])[CH2:68][CH2:69][CH2:70][CH2:71][NH:72][C:73]([O:75][C:76]([CH3:78])([CH3:77])[CH3:79])=[O:74])=[O:55])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 10868DicyclohexylcarbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 13753067HCID 13753067, compoundHCID 131715273HCID 131715273, compound

Product 1

HCID 131715272Z-D-Lys(Boc)-Phe-D-Lys(Boc)-Phe-Gly-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.6 g of HOOBt, 1.3 g of NEM and 2.2 g of DCC are added to 5.3 g of Z-D-Lys(Boc)-Phe-OH and 6.4 g of H-D-Lys(Boc)-Phe-Gly-OMe, TosOH in 100 ml of DMF, with stirring. After the mixture has been left to stand overnight and the urea has been filtered off, the solvent is distilled off in vacuo. The residue is taken up in 300 ml of ethyl acetate/n-butanol (2:1), the mixture is washed, as above, with citric acid solution, sodium bicarbonate solution and water and dried over sodium sulfate and the solvent is distilled off in vacuo. The residue is recrystallized from 60 ml of isopropanol.

Workup

  1. waitAfter the mixture has been left
  2. filtrationthe urea has been filtered off
  3. distillationthe solvent is distilled off in vacuo
  4. washthe mixture is washed
  5. dry with materialas above, with citric acid solution, sodium bicarbonate solution and water and dried over sodium sulfate
  6. distillationthe solvent is distilled off in vacuo
  7. customThe residue is recrystallized from 60 ml of isopropanol

Sources & evidence

ORD record
ord-898f37a67c364125a2bb64fdd0ef329e
Source dataset
uspto-grants-1987_09
Patent number
US04696913

Reaction notes

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