HCID 178491770, compound → HCID 178448167, compound

HRID 1457524Notes

Reaction equation

HRID 1457524 reaction equation
[NH:1]1[C:55](=[O:56])[C@@H:51]([CH:52]([CH3:54])[CH3:53])[NH:50][C:48](=[O:49])[C@H:40]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[NH:39][C:37](=[O:38])[C@H:32]([CH2:33][C:34](=[O:36])[OH:35])[NH:31][C:29](=[O:30])[CH2:28][CH2:27][NH:26][C:24](=[O:25])[C@@H:2]1[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:23])[NH:8]S(C1C(C)=C(C)C(OC)=CC=1C)(=O)=O>C(O)(C(F)(F)F)=O.ClCCl.C1(S)C=CC=CC=1>[NH:1]1[C:55](=[O:56])[C@@H:51]([CH:52]([CH3:54])[CH3:53])[NH:50][C:48](=[O:49])[C@H:40]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[NH:39][C:37](=[O:38])[C@H:32]([CH2:33][C:34](=[O:35])[OH:36])[NH:31][C:29](=[O:30])[CH2:28][CH2:27][NH:26][C:24](=[O:25])[C@@H:2]1[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:23]

Participants

5

Reactant 1

HCID 178491770HCID 178491770, compound

Product 1

HCID 178448167HCID 178448167, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 7969ThiophenolSolvent

Procedure

A solution of 0.28 g of cyclo-(Arg(Mtr)-β-Ala-Asp-Phe-D-Val) [obtainable by cyclization according to Ex. 1] in 8.4 ml of TFA, 1.7 ml of dichloromethane and 0.9 ml of thiophenol is allowed to stand at room temperature for 4 hours, then concentrated and, after diluting with water, freeze-dried. Gel filtration on Sephadex G 10 (acetic acid/water 1:1) and subsequent purification by preparative HPLC under the conditions indicated give cyclo-(Arg-β-Ala-Asp-Phe-D-Val); RT=17.0; M+ 589.

Workup

  1. concentrationconcentrated
  2. additionafter diluting with water
  3. customfreeze-dried
  4. filtrationGel filtration
  5. customon Sephadex G 10 (acetic acid/water 1:1) and subsequent purification by preparative HPLC under the conditions

Sources & evidence

ORD record
ord-b1dcda73c2384a4c86c928f24ff719f2
Source dataset
uspto-grants-1998_12
Patent number
US05849692

Reaction notes

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