Hydrochloric Acid → HCID 178512879, compound

HRID 1194988Notes

Reaction equation

HRID 1194988 reaction equation
Cl.CC(O)=O.[NH:6]([C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[C@@H:7]([C:19]([NH:21][C@H:22]([C:30]([NH:32][C@H:33]([C:41]([OH:43])=[O:42])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:40])[NH2:39])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:20])[CH2:8][CH2:9][CH2:10][NH:11]C(OC(C)(C)C)=O.Cl>>[NH:6]([C:44]([O:46][CH2:47][C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)=[O:45])[C@@H:7]([C:19]([NH:21][C@H:22]([C:30]([NH:32][C@H:33]([C:41]([OH:43])=[O:42])[CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:40])=[O:31])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:20])[CH2:8][CH2:9][CH2:10][NH2:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 22641269Acetate-hydrochloric acidHCID 178453440HCID 178453440, compound

Product 1

HCID 178512879HCID 178512879, compoundYield 102.6%

Procedure

Into 5.2 ml (10.4 mmoles) of 2N HCl/AcOH was dissolved 2.3 g (2.6 mmoles) of Z-D-Orn(BOC)-Phe-Arg-CHA.HCl. After reacting it at room temperature for 2 hours, the product was precipitated in dry ether and the deposited crystalline product was collected by filtration and dried. Thus, crude Z-D-Orn-Phe-Arg-CHA.2HCl was obtained. It was purified by means of Toyopearl HW40F column with 30% AcOH as a developing solvent. Thus, 1.52 g (74.9%) of Z-D-Orn-Phe-Arg-CHA.2HCl was obtained.

Workup

  1. customat room temperature
  2. customfor 2 hours
  3. customthe product was precipitated in dry ether
  4. filtrationthe deposited crystalline product was collected by filtration
  5. customdried
  6. customThus, crude Z-D-Orn-Phe-Arg-CHA.2HCl was obtained
  7. customIt was purified by means of Toyopearl HW40F column with 30% AcOH as a developing solvent

Sources & evidence

ORD record
ord-a793e7545a664ebc96f16f9a5f3cf447
Source dataset
uspto-grants-1989_03
Patent number
US04816562

Reaction notes

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