HCID 58611852, compound → HCID 10046348, compound

HRID 2375216Notes

Reaction equation

HRID 2375216 reaction equation
C([O:8][NH:9][C:10]([C:12]1[CH:36]=[CH:35][C:15]([O:16][C:17]([C:19]2([C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=3)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])=[CH:14][CH:13]=1)=[O:11])C1C=CC=CC=1>[Pd].CO.C(OCC)C>[OH:8][NH:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]([C:19]2([C:25]3[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=3)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)=[O:18])=[CH:35][CH:36]=1)=[O:11]

Participants

5

Reactant 1

HCID 58611852HCID 58611852, compound

Product 1

HCID 10046348HCID 10046348, compoundYield 64.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 4-{1-[(4-{[(benzyloxy)amino]carbonyl}phenoxy)carbonyl] cyclohexyl)-benzoate (E23) (0.063 g, 0.129 mmol) and 5% palladium on activated carbon (0.026 g) in methanol (1 ml) was hydrogenated at room temperature for 50 minutes. The black suspension was filtered, the catalyst was washed with methanol (3×1 ml), and the filtrate was evaporated to give a viscous oil. The oil was converted to white crystals by stirring in diethyl ether (3 ml) overnight. The solid was filtered, washed with diethyl ether (0.5 ml), and dried in vacuum to give the title compound (0.033 g, 64%) as white crystals, m.p. 129-131° C. 1H NMR (DMSO-d6, HMDSO) δ: 1.13-1.99 (8H, m); 2.35-2.58 (2H, m, overlapped with a signal of DMSO); 3.86 (3H, s); 7.05 (2H, d, J=8.6 Hz); 7.65 (2H, d, J=8.4 Hz); 7.77 (2H, d, J=8.6 Hz); 8.01 (2H, d, J=8.4 Hz); 9.07 (1H, s); 11.25 (1H, s). HPLC analysis on Symmetry C8 column: impurities 2.5% (column size 3.9×150 mm; mobile phase acetonitrile−0.1M phosphate buffer (pH 2.5), 60:40; detector UV 254 nm; sample concentration 0.5 mg/ml; flow rate 1.0 ml/min). Anal. Calcd for C22H23NO6*0.35H2O, %: C, 65.45; H, 5.92; N, 3.47. Found, %: C, 65.17; H, 5.76; N, 3.49.

Workup

  1. filtrationThe black suspension was filtered
  2. washthe catalyst was washed with methanol (3×1 ml)
  3. customthe filtrate was evaporated
  4. customto give a viscous oil
  5. filtrationThe solid was filtered
  6. washwashed with diethyl ether (0.5 ml)
  7. customdried in vacuum

Sources & evidence

ORD record
ord-546ccc2a479f4353a17b47f4c1f8ddfb
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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