Hydrogen Bromide → H-Lys-Gln-Nle-Ala-Val-Lys-NH2

HRID 649094Notes

Reaction equation

HRID 649094 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:18]([NH:20][C@H:21]([C:27]([NH:29][C@H:30]([C:35]([NH:37][C@H:38]([C:40]([NH:42][C@H:43]([C:47]([NH:49][C@H:50]([C:66]([NH2:68])=[O:67])[CH2:51][CH2:52][CH2:53][CH2:54][NH:55]C(OCC1C=CC=CC=1)=O)=[O:48])[CH:44]([CH3:46])[CH3:45])=[O:41])[CH3:39])=[O:36])[CH2:31][CH2:32][CH2:33][CH3:34])=[O:28])[CH2:22][CH2:23][C:24](=[O:26])[NH2:25])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1)=O.Br>C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]([C:18]([NH:20][C@H:21]([C:27]([NH:29][C@H:30]([C:35]([NH:37][C@H:38]([C:40]([NH:42][C@H:43]([C:47]([NH:49][C@H:50]([C:66]([NH2:68])=[O:67])[CH2:51][CH2:52][CH2:53][CH2:54][NH2:55])=[O:48])[CH:44]([CH3:46])[CH3:45])=[O:41])[CH3:39])=[O:36])[CH2:31][CH2:32][CH2:33][CH3:34])=[O:28])[CH2:22][CH2:23][C:24](=[O:26])[NH2:25])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 131715498HCID 131715498, compound

Product 1

HCID 131715499H-Lys-Gln-Nle-Ala-Val-Lys-NH2

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The protected hexapeptide (XV) (0.2 g, 0.2 mmol) was dissolved in TFA (5 ml) and treated with HBr gas over 1 hr. The mixture was evaporated in vacuo and triturated with Et2O (2×50 ml) to give (V) as a hydrobromide salt (0.13 g) RfH=0.14. This and a subsequent batch of product were purified by adsorption on to an ion exchange column (CM 25 Sephadex, Pharmacia) which was washed with 10-100 mmol NH4OAc at pH 7. The product was eluted with 100 mmol NH4OAc at pH 8.5. Lyophilisation and subsequent preparative HPLC [μBondapak ODS.; CH3CN: 50 mmol NH4OAc(aq) (15:85) gave (V) as an acetate salt (0.15 g) mp 253°-255° C. T.l.c. RfH=0.14, MH+ (FAB)=685.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customtriturated with Et2O (2×50 ml)

Sources & evidence

ORD record
ord-419a1a77aa544e0394b4b50a4543464f
Source dataset
uspto-grants-1988_04
Patent number
US04737487

Reaction notes

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