HCID 70039904, compound → HCID 178462211, compound

HRID 280787Notes

Reaction equation

HRID 280787 reaction equation
[CH2:1]([P:8]([NH:17][C@H:18]([C:20]([N:22]([CH:34]1[CH2:42][C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:35]1)[CH2:23][C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([OH:30])=[O:29])=[O:25])=[O:21])[CH3:19])([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:43][C@H:44]([C:52]([OH:54])=[O:53])[CH2:45][CH2:46][CH2:47][NH:48][C:49](=[NH:51])[NH2:50]>C(O)C.O>[NH2:43][C@H:44]([C:52]([OH:54])=[O:53])[CH2:45][CH2:46][CH2:47][NH:48][C:49](=[NH:50])[NH2:51].[CH2:1]([P:8]([NH:17][C@H:18]([C:20]([N:22]([CH:34]1[CH2:35][C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:42]1)[CH2:23][C:24]([N:26]1[CH2:33][CH2:32][CH2:31][C@H:27]1[C:28]([OH:30])=[O:29])=[O:25])=[O:21])[CH3:19])([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70039904HCID 70039904, compoundHCID 178418600HCID 178418600, compound

Product 1

HCID 178462211HCID 178462211, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Dibenzylphosphoryl-L-alanyl-N-(2-indanyl)-glycyl-L-proline (0.77 g, 1.2 m mole) was dissolved in ethanol (4 ml), and the aqueous solution produced by dissolving L-arginine (0.25 g, 1.2 m mole) in water (4 ml), was added thereto. The solvent was distilled off under reduced pressure, and then water was added thereto. This water solution was freeze-dried to obtain dibenzylphosphoryl-L-alanyl-N-(2-indanyl)glycyl-L-proline L-arginine salt (0.84 g, yield: 85.2%). This product gave a single spot having an Rf =0.2 for the peptide in free form, and an Rf =0 for arginine, respectively, by thin layer chromatography (developing solvent, acetonitrile:acetic acid=30:1, Colour forming method: spraying of 25% hydrobromic acid and 0.1% ninhydrine, and heating).

Workup

  1. customthe aqueous solution produced
  2. additionwas added
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionwater was added
  5. dry with materialThis water solution was freeze-dried

Sources & evidence

ORD record
ord-ac01f0377d31454eb32e882eb97bcfb0
Source dataset
uspto-grants-1986_05
Patent number
US04590178

Reaction notes

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