HCID 57751157, compound → HCID 67495519, compound

HRID 658564Notes

Reaction equation

HRID 658564 reaction equation
C(OC([NH:11][N:12]([C@@H:23]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH2:24][CH:25]=[CH2:26])[C:13](=[O:22])[C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=1)=O)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[CH:27]1([C@H:23]([N:12]([C:13](=[O:22])[C:14]2[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=2)[NH2:11])[CH2:24][CH2:25][CH3:26])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 1

HCID 57751157HCID 57751157, compound

Product 1

HCID 67495519HCID 67495519, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent3×

Procedure

(R)—N′-(1-Cyclohexyl-but-3-enyl)-N′-(3,5-dimethyl-benzoyl)-hydrazine carboxylic acid benzyl ester (2.91 g, 6.7 mmoles) was suspended in ca. 50 mL glacial acetic acid. 102 mg 10% palladium on charcoal was added as a slurry in several mL of acetic acid. The mixture was diluted with acetic acid to 75 mL, and shaken on a Parr hydrogenator for 90 minutes at 20-30 psi. The suspension was allowed to stand for two days to allow the carbon to settle out. The supernatant was filtered through a 0.45 micron syringe filter into a recrystallizing dish and solvent was evaporated to leave 2.06 g (102% mass balance) of (R)-3,5-dimethyl-benzoic acid N-(1-cyclohexyl-butyl)-hydrazide as a reddish brown viscous oil. Rf=0.24 (2:1 hexanes:ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 7.05 (1H, s), 7.0 (2H, s), 4.55+3.35 (1H, 2 t), 2.4 (6H, s), 0.8-1.9 (15H, m), 0.9 (3H, t); HRMS (ESI) m/z calcd for C19H31N2O [M+H]+ 303.2436, found 303.2441, calcd for C19H30N2NaO [M+Na]+ 325.2256, found 325.2262.

Workup

  1. waitto stand for two days
  2. filtrationThe supernatant was filtered through a 0.45 micron syringe
  3. filtrationfilter into a recrystallizing dish and solvent
  4. customwas evaporated

Sources & evidence

ORD record
ord-3ec589da886f40468b717688d258e9f1
Source dataset
uspto-grants-2011_12
Patent number
US08076517B2

Reaction notes

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