HCID 178476536, compound → HCID 178476511, compound

HRID 1086121Notes

Reaction equation

HRID 1086121 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:33]([NH:35][C@H:36]([C:44]([N:46]1[CH2:57][CH2:56][CH2:55][C@H:47]1[C:48]([O:50]C(C)(C)C)=[O:49])=[O:45])[CH2:37][CH2:38][CH2:39][NH:40][C:41](=[NH:43])[NH2:42])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28]C(C)(C)C)=[CH:24][CH:23]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[CH3:58][C:59]([OH:61])=[O:60].[CH3:62][C:63]([OH:65])=[O:64].CC(O)=O>FC(F)(F)C(O)=O.C(S)C>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:17]([NH:19][C@H:20]([C:33]([NH:35][C@H:36]([C:44]([N:46]1[CH2:57][CH2:56][CH2:55][C@H:47]1[C:48]([OH:50])=[O:49])=[O:45])[CH2:37][CH2:38][CH2:39][NH:40][C:41](=[NH:42])[NH2:43])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)=[O:18])[CH:14]([CH3:15])[CH3:16])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9].[CH3:58][C:59]([OH:61])=[O:60].[CH3:62][C:63]([OH:65])=[O:64]

Participants

4

Reactant 1

HCID 178476536HCID 178476536, compound

Product 1

HCID 178476511HCID 178476511, compound

Reagents, catalysts & solvents 2

HCID 6343EthanethiolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

670 mg of H-Arg-Val-Tyr(tBu)-Arg-Pro-OtBu triacetate are dissolved in a mixture of 10 ml of 90% trifluoroacetic acid and 1 ml of ethyl mercaptan. The solution is left to stand at room temperature for one hour, and is concentrated in vacuo. The residue is partitioned between water and tert.butyl methyl ether. The aqueous phase is stirred with a weakly basic ion exchanger (acetate form) until the pH has become 3.5-4.0. The ion exchanger is filtered off with suction, and the filtrate is freeze-dried.

Workup

  1. waitThe solution is left
  2. concentrationis concentrated in vacuo
  3. customThe residue is partitioned between water and tert.butyl methyl ether
  4. filtrationThe ion exchanger is filtered off with suction
  5. customthe filtrate is freeze-dried

Sources & evidence

ORD record
ord-830b804a8dba43aca7469f0ff030aa61
Source dataset
uspto-grants-1991_04
Patent number
US05011825

Reaction notes

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