HCID 178448348, compound → HCID 178476271, compound

HRID 904963Notes

Reaction equation

HRID 904963 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:26]([NH:28][C@H:29]([C:39]([NH:41][C@H:42]([C:46]([NH:48][C@H:49]([C:62]([O:64]C(C)(C)C)=[O:63])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57]C(C)(C)C)=[CH:53][CH:52]=1)=[O:47])[CH:43]([CH3:45])[CH3:44])=[O:40])[CH2:30][CH2:31][C:32](=[O:38])[O:33]C(C)(C)C)=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][NH:18]C(OC(C)(C)C)=O)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].Cl.Cl>FC(F)(F)C(O)=O.C(S)C>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:26]([NH:28][C@H:29]([C:39]([NH:41][C@H:42]([C:46]([NH:48][C@H:49]([C:62]([OH:64])=[O:63])[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([OH:57])=[CH:53][CH:52]=1)=[O:47])[CH:43]([CH3:44])[CH3:45])=[O:40])[CH2:30][CH2:31][C:32](=[O:33])[OH:38])=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9].[CH3:31][C:32]([OH:38])=[O:33]

Participants

4

Reactant 1

HCID 178448348HCID 178448348, compound

Product 1

HCID 178476271HCID 178476271, compound

Reagents, catalysts & solvents 2

HCID 6343EthanethiolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1 g of H-Arg-Lys(Boc)-Glu(OBut)-Val-Tyr(But)-OBut.2HCl (0.966 mmole) is dissolved in a mixture of 10 ml of trifluoroacetic acid and 1 ml of ethylmercaptan. The mixture is allowed to stand for one hour at room temperature and is concentrated. The residue is dissolved again in a little methanol and the solution is concentrated once more. The residue is dissolved in water, insoluble matter is filtered off and the solution is chromatographed over a strongly basic exchanger in the acetate form. The eluate is concentrated and purified further by being chromatographed on a hydroxypropylated crosslinked dextran gel in a water/acetic acid/n-butanol mixture. Yield 491 mg (57%), [α]D =-21.8° (c=1, water). Aminoacid analysis: Glu 1.00, Val 0.97, Tyr 0.92, Lys 1.03 and Arg 0.99. Protein content: 82%.

Workup

  1. concentrationis concentrated
  2. dissolutionThe residue is dissolved again in a little methanol
  3. concentrationthe solution is concentrated once more
  4. dissolutionThe residue is dissolved in water
  5. filtrationinsoluble matter is filtered off
  6. customthe solution is chromatographed over a strongly basic exchanger in the acetate form
  7. concentrationThe eluate is concentrated
  8. custompurified further
  9. customby being chromatographed on a hydroxypropylated crosslinked dextran gel in a water/acetic acid/n-butanol mixture
  10. customYield 491 mg (57%), [α]D =-21.8° (c=1, water)

Sources & evidence

ORD record
ord-9fd04dfb137d40e59494400eeb1aac60
Source dataset
uspto-grants-1983_12
Patent number
US04420424

Reaction notes

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