HCID 178491769, compound → HCID 178512832, compound

HRID 365273Notes

Reaction equation

HRID 365273 reaction equation
[NH:1]1[C:51](=[O:52])[C@H:50]2[CH2:53][CH2:54][CH2:55][CH2:56][N:49]2[C:47](=[O:48])[C@@H:39]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[NH:38][C:36](=[O:37])[C@H:31]([CH2:32][C:33](=[O:35])[OH:34])[NH:30][C:28](=[O:29])[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:51](=[O:52])[C@H:50]2[CH2:53][CH2:54][CH2:55][CH2:56][N:49]2[C:47](=[O:48])[C@@H:39]([CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[NH:38][C:36](=[O:37])[C@H:31]([CH2:32][C:33](=[O:34])[OH:35])[NH:30][C:28](=[O:29])[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 178491769HCID 178491769, compound

Product 1

HCID 178512832HCID 178512832, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 7969ThiophenolSolvent

Procedure

A solution of 0.28 g of cyclo-(Arg(Mtr)-Gly-Asp-DPhe-DhPro) [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 the residue is diluted with water and then 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-Gly-Asp-DPhe-DhPro); FAB-MS (M+H): 587.

Workup

  1. concentrationconcentrated
  2. additionthe residue is diluted 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-53d747954d004fbbba3a335d5c7402ac
Source dataset
uspto-grants-2000_10
Patent number
US06127335

Reaction notes

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