HCID 178453397, compound → HCID 178512883, compound

HRID 1154159Notes

Reaction equation

HRID 1154159 reaction equation
[NH:1]([C:65]([O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:66])[C@@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@@H:29]([C:37]([NH:39][C@H:40]([C:51]([N:53]1[CH2:64][CH2:63][CH2:62][C@H:54]1[C:55]([O:57]C(C)(C)C)=[O:56])=[O:52])[CH2:41][C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[NH:44][CH:43]=1)=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[NH:25])[NH2:24])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OC(C)(C)C)=O>FC(F)(F)C(O)=O.C(S)C>[NH:1]([C:65]([O:67][CH2:68][C:69]1[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=1)=[O:66])[C@@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@@H:29]([C:37]([NH:39][C@H:40]([C:51]([N:53]1[CH2:64][CH2:63][CH2:62][C@H:54]1[C:55]([OH:57])=[O:56])=[O:52])[CH2:41][C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[NH:44][CH:43]=1)=[O:38])[CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:27])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[NH:24])[NH2:25])=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

4

Reactant 1

HCID 178453397HCID 178453397, compound

Product 1

HCID 178512883HCID 178512883, compound

Reagents, catalysts & solvents 2

HCID 6343EthanethiolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1.55 g of Z-D-Lys(Boc)-Arg-D-Phe-Trp-Pro-OBut are dissolved in 14.5 ml of 90 percent strength trifluoroacetic acid and 1.5 ml of ethyl mercaptan. The solution is left to stand for 1 hour at room temperature and is concentrated. The residue is dissolved in water and chromatographed over a weakly basic ion exchanger (acetate form). The eluate is freeze-dried. Yield 883 mg. The peptide is purified by being chromatographed in 90 percent strength methanol over a crosslinked, hydroxypropylated dextran gel. Yield 570 mg, [α]D22 =-24.6° (c=1, methanol).

Workup

  1. waitThe solution is left
  2. concentrationis concentrated
  3. dissolutionThe residue is dissolved in water
  4. customchromatographed over a weakly basic ion exchanger (acetate form)
  5. customThe eluate is freeze-dried
  6. customThe peptide is purified
  7. customby being chromatographed in 90 percent strength methanol over a crosslinked, hydroxypropylated dextran gel
  8. customYield 570 mg, [α]D22 =-24.6° (c=1, methanol)

Sources & evidence

ORD record
ord-2a2e8d4556d04ad4a0a5d48aa37351a3
Source dataset
uspto-grants-1984_12
Patent number
US04487764

Reaction notes

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