Hydrochloric Acid → HCID 178451298, compound

HRID 2293058Notes

Reaction equation

C1CCC(N=C=NC2CCCCC2)CC1.[NH:16]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C@H:17]([C:25]([OH:27])=O)[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:24])[NH2:23].Cl.[NH2:39][CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42].C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:16]([C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[C@H:17]([C:25]([NH:39][CH2:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[O:27])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:24])[NH2:23]

Participants

Conditions

Temperature: 0 °C

Procedure

39.6 g of DCC are added at 0° C. to a solution of 55 g of Z-Arg-OH, 30.18 g of HCl.H-Gly-OtBu and 24.3 g of HOBt in 400 ml of dimethylformamide. The mixture is left to stir at 0° C. for 1 hour and at room temperature for 3 hours and to stand at room temperature overnight. The DC-urea is filtered off with suction and the filtrate is concentrated. The residue is subjected to countercurrent partition between ethyl acetate and saturated NaHCO3 solution (400 ml each). This results in the required substance precipitating in the first separating funnel after the 3rd stage.

Workup

waitThe mixture is left
waitto stand at room temperature overnight
filtrationThe DC-urea is filtered off with suction
concentrationthe filtrate is concentrated
customto countercurrent partition between ethyl acetate and saturated NaHCO3 solution (400 ml each)
customThis results in the required substance
customprecipitating in the first separating funnel after the 3rd stage

Sources & evidence

ORD record: ord-65e4ab212991494b94d47f6c0770681e
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686421

Reaction notes

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