Hydrochloric Acid → HCID 136338593, compound

HRID 1297245Notes

Reaction equation

HRID 1297245 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1([C:16]2[NH:20][C:19](=[O:21])[O:18][N:17]=2)[CH2:11][CH:10]1[CH2:12][CH:13]([CH3:15])[CH3:14])(C)(C)C.[ClH:23]>O1CCOCC1.CCOCC>[ClH:23].[NH2:7][CH2:8][C:9]1([C:16]2[NH:20][C:19](=[O:21])[O:18][N:17]=2)[CH2:11][CH:10]1[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136338592HCID 136338592, compound

Product 1

HCID 136338593HCID 136338593, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of {2-isobutyl-1-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-cyclopropylmethyl}-carbamic acid tert-butyl ester (4.2 g, 13.5 mmol) in dry 1,4-dioxane (20 ml) was added 4N HCl (40 mL, in 1,4-dioxane). The reaction mixture was stirred at room temperature overnight and diluted with ether (100 mL). The precipitate was collected and washed with ether and dried to give 2.6 g (79%) of 3-(1-aminomethyl-2-isobutyl-cyclopropyl)-4H-[1,2,4]oxadiazol-5-one hydrochloride as a white solid: mp: 181-182° C.; 1H NMR (300 MHz, D2O) δ 0.94-0.98 (m, 6H), 1.21 (m, 1H), 1.35 (m, 1H), 1.58 (m, 3H), 1.73 (m, 1H), 3.24 (d, J=14.2 Hz, 1H), 3.71 (d, J=14.3 Hz, 1H); 13C NMR (75 MHz, D2O) δ 19.3, 19.6, 21.8, 22.1, 26.6, 28.2, 36.7, 39.5, 162.2, 162.6; MS (APCI) m/z 212 [M+H]+. Anal. Calc'd For C10H17N3O2—HCl: C, 48.49; H, 7.32; N, 16.96; Cl, 14.31. Found: C, 48.49; H, 7.17; N, 16.84; Cl, 13.94.

Workup

  1. customThe precipitate was collected
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-e56b6e04ac2840b1a2bac37a32bd2029
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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