Hydrochloric Acid → HCID 178427480, compound

HRID 1194990Notes

Reaction equation

HRID 1194990 reaction equation
Cl.CC(O)=O.[NH:6]([S:45]([C:48]1[CH:54]=[CH:53][C:51]([CH3:52])=[CH:50][CH:49]=1)(=[O:47])=[O:46])[C@@H:7]([C:20]([NH:22][C@H:23]([C:31]([NH:33][C@H:34]([C:42]([OH:44])=[O:43])[CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:41])[NH2:40])=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])[CH2:8][CH2:9][CH2:10][CH2:11][NH:12]C(OC(C)(C)C)=O.Cl>>[NH:6]([S:45]([C:48]1[CH:49]=[CH:50][C:51]([CH3:52])=[CH:53][CH:54]=1)(=[O:47])=[O:46])[C@@H:7]([C:20]([NH:22][C@H:23]([C:31]([NH:33][C@H:34]([C:42]([OH:44])=[O:43])[CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:40])[NH2:41])=[O:32])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:21])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 22641269Acetate-hydrochloric acidHCID 178427481HCID 178427481, compound

Product 1

HCID 178427480HCID 178427480, compoundYield 131.8%

Procedure

Into 1.7 ml (3.5 mmoles) of 2N HCl/AcOH was dissolved 0.77 g (0.88 mmoles) of Tos-D-Lys(BOC)-Phe-Arg-CHA.HCl. After reacting it at room temperature for 2 hours, the reaction mixture was reprecipitated in dry ether and the deposited crystalline product was collected by filtration and dried. Thus, 0.70 g of crude Tos-D-Lys-Phe-Arg-CHA.2HCl was obtained. It was purified by means of Toyopearl HW40F column with 30% AcOH as a developing solvent. Thus, 0.48 g (67.6%) of Tos-D-Lys-Phe-Arg-CHA.2HCl was obtained.

Workup

  1. customat room temperature
  2. customfor 2 hours
  3. customthe reaction mixture was reprecipitated in dry ether
  4. filtrationthe deposited crystalline product was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-5972aa9ea124400299872f8c5e94a2b3
Source dataset
uspto-grants-1989_03
Patent number
US04816562

Reaction notes

Loading…