Guanidine → HCID 178422469, compound

HRID 1460437Notes

Reaction equation

[NH2:1][C:2]([NH2:4])=[NH:3].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[C:12]([NH:16][C:17]([CH:19]1[CH2:21][C:20]1([CH3:23])[CH3:22])=[O:18])[C:13]([OH:15])=[O:14]>O>[CH3:22][C:20]1([CH3:23])[CH2:21][CH:19]1[C:17]([NH:16]/[C:12](=[CH:11]\[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:3][C:2]([NH2:4])=[NH:1])/[C:13]([OH:15])=[O:14])=[O:18]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 2 mmoles of guanidine (prepared from 432 mg of guanidine sulfate and 630 mg of barium hydroxide octahydrate) in 7 ml of water was added 332 mg (1 mmole) of 8-bromo-2-(2,2-dimethylcyclopropanecarboxamido)-2-octenoic acid, and the solution was heated at 70° C. in a nitrogen atmosphere for 1 hr. The reaction mixture was applied to a 2×25 cm column of Dowex 50W-X8 (H+, 100-200 mesh). After elution with water the fractions containing the product were pooled and evaporated under reduced pressure. The residue was dissolved in several ml of warm ethanol and added dropwise to 100 ml of ether with rapid stirring. Filtration and washing with ether gave 107 mg of Z-2-(2,2-dimethylcyclopropanecarboxamido)-8-guanidino-2-octenoic acid as an amorphous electrostatic powder. Homogeneous by TLC (n-BuOH, HOAc, H2O; 4:1:1). NMR (D2O, NaOD): 6.48δ t, 1H, ##STR76## 3.10δ (m, 2H, ##STR77## 2.10δ (m, 2H, ##STR78## 1.17δ (s, 3H, ##STR79## 1.12δ (s, 3H, ##STR80##

Workup

washAfter elution with water the fractions
additioncontaining the product
customevaporated under reduced pressure
dissolutionThe residue was dissolved in several ml of warm ethanol
additionadded dropwise to 100 ml of ether with rapid stirring
filtrationFiltration
washwashing with ether

Sources & evidence

ORD record: ord-0df68b40ea1e4545b1ef555ef02cbba9
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05071843

Reaction notes

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