Triethylamine → (2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N'-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide

HRID 1242546Notes

Reaction equation

HRID 1242546 reaction equation
C(N(CC)CC)C.[C:8]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:13]=[CH:12][C:11]([C:14]([N:16]2[CH2:20][C:19](=[N:21][O:22][CH3:23])[CH2:18][C@H:17]2[C:24]#[N:25])=[O:15])=[CH:10][CH:9]=1.Cl.[NH2:33][OH:34]>C(O)C>[C:8]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:9]=[CH:10][C:11]([C:14]([N:16]2[CH2:20][C:19](=[N:21][O:22][CH3:23])[CH2:18][C@H:17]2[C:24](=[N:33][OH:34])[NH2:25])=[O:15])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 131725967(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-4-(methoxyimino)-2-pyrrolidinecarbonitrile

Product 1

HCID 90995821(2S,4EZ)-1-([1,1'-biphenyl]-4-ylcarbonyl)-N'-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamideYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the general method outlined above for the synthesis of Intermediates 8, triethylamine (1.94 ml, 13.94 mmol) was slowly added to a suspension of (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-4-(methoxyimino)-2-pyrrolidinecarbonitrile (3.71 g, 11.62 mmol) and hydroxylamine.hydrochloride (0.97 g, 13.94 mmol) in ethanol (150 ml), under stirring. The reaction mixture was allowed to stir at 80° C. for 16 h, and then cooled to ambient temperatures. The solvent was removed by evaporation and the solid was suspended in water (100 ml) then filtered. The solid was washed with diethyl ether (2×100 ml) whilst on the sinter and then dried in vacuo at 40° C., to give the desired product, (2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-N′-hydroxy-4-(methoxyimino)-2-pyrrolidinecarboximidamide (3.35 g, 82%).

Workup

  1. stirringto stir at 80° C. for 16 h
  2. temperaturecooled to ambient temperatures
  3. customThe solvent was removed by evaporation
  4. filtrationthen filtered
  5. washThe solid was washed with diethyl ether (2×100 ml) whilst on the sinter
  6. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-8a1e997bb74f47ce8e12a8f171205832
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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