HCID 58611832, compound → HCID 10088563, compound

HRID 2375215Notes

Reaction equation

HRID 2375215 reaction equation
[C:1]1([C:7]2([C:13]([O:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]([NH:24][O:25]CC4C=CC=CC=4)=[O:23])=[CH:18][CH:17]=3)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].CO>[C:1]1([C:7]2([C:13]([O:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]([NH:24][OH:25])=[O:23])=[CH:20][CH:21]=3)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 58611832HCID 58611832, compound

Product 1

HCID 10088563HCID 10088563, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-{[(benzyloxy)amino]carbonyl}phenyl 1-phenylcyclohexane-carboxylate (E22) (0.054 g, 0.125 mmol) and 5% palladium on activated carbon (0.038 g) in methanol (1 ml) was hydrogenated at room temperature for 45 minutes. The black suspension was filtered, the catalyst was washed with methanol (3×1 ml), and the filtrate was evaporated and dried in vacuum to give the title compound (0.038 g, 89%) as white crystals, m.p. 142-144° C. 1H NMR (DMSO-d6, HMDSO) δ: 1.16-1.94 (8H, m); 2.35-2.64 (2H, m, overlapped with a signal of DMSO); 7.02 (2H, d, J=8.7 Hz); 7.26-7.54 (5H, m); 7.77 (2H, d, J=8.7 Hz); 9.06 (1H, s); 11.24 (1H, br s). HPLC analysis on Symmetry C8 column: impurities 2% (column size 3.9×150 mm; mobile phase acetonitrile−0.1M phosphate buffer (pH 2.5), 50:50; detector UV 230 nm; sample concentration 0.5 mg/ml; flow rate 1.1 ml/min). Anal. Calcd for C20H21NO4*0.4H2O, %: C, 69.31; H, 6.34; N, 4.04. Found, %: C, 69.36; H, 6.24; N, 3.97.

Workup

  1. filtrationThe black suspension was filtered
  2. washthe catalyst was washed with methanol (3×1 ml)
  3. customthe filtrate was evaporated
  4. customdried in vacuum

Sources & evidence

ORD record
ord-7597274e4eb840f9a816b0ab80dfb956
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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