HCID 178453396, compound → HCID 178476579, compound

HRID 1154155Notes

Reaction equation

HRID 1154155 reaction equation
[NH:1]([C:76]([O:78][CH2:79][C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1)=[O:77])[C@H:2]([C:15]([NH:17][C@H:18]([C:31]([NH:33][C@H:34]([C:47]([NH:49][C@H:50]([C:58]([NH:60][C@H:61]([C:69]([O:71]C(C)(C)C)=[O:70])[CH2:62][CH2:63][CH2:64][NH:65][C:66](=[NH:68])[NH2:67])=[O:59])[CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)=[O:48])[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42]C(C)(C)C)=[CH:38][CH:37]=1)=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23]C(OC(C)(C)C)=O)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OC(C)(C)C)=O>FC(F)(F)C(O)=O>[NH:1]([C:76]([O:78][CH2:79][C:80]1[CH:81]=[CH:82][CH:83]=[CH:84][CH:85]=1)=[O:77])[C@H:2]([C:15]([NH:17][C@H:18]([C:31]([NH:33][C@H:34]([C:47]([NH:49][C@H:50]([C:58]([NH:60][C@H:61]([C:69]([OH:71])=[O:70])[CH2:62][CH2:63][CH2:64][NH:65][C:66](=[NH:67])[NH2:68])=[O:59])[CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)=[O:48])[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1)=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].[CH3:61][C:69]([OH:71])=[O:70].[CH3:61][C:69]([OH:71])=[O:70]

Participants

3

Reactant 1

HCID 178453396HCID 178453396, compound

Product 1

HCID 178476579HCID 178476579, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1.6 g of Z-Lys(Boc)-Lys(Boc)-Tyr(But)-Phe-Arg-OBut are dissolved in 15 ml of 90% strength trifluoroacetic acid. The solution is left to stand at room temperature for 1 hour and is concentrated. The residue is triturated with ether and is suction-drained. The residue is then dissolved in water and chromatographed over a weakly basic ion exchanger (acetate form). The eluate is concentrated and chromatographed in 90% strength methanol over a crosslinked, hydroxypropylated dextran gel. Yield 920 mg, [α]D24 =-29.7° (c=1, methanol).

Workup

  1. waitThe solution is left
  2. concentrationis concentrated
  3. customThe residue is triturated with ether
  4. dissolutionThe residue is then dissolved in water
  5. customchromatographed over a weakly basic ion exchanger (acetate form)
  6. concentrationThe eluate is concentrated
  7. customchromatographed in 90% strength methanol over a crosslinked, hydroxypropylated dextran gel
  8. customYield 920 mg, [α]D24 =-29.7° (c=1, methanol)

Sources & evidence

ORD record
ord-e23319dfb7cb47489ebd61ee1578e910
Source dataset
uspto-grants-1984_12
Patent number
US04487764

Reaction notes

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