4-{[(Benzyloxy)amino]carbonyl}phenyl 1-(4-methoxyphenyl)cyclohexanecarboxylate → 4-[(Hydroxyamino)carbonyl]phenyl 1-(4-methoxyphenyl)-cyclohexanecarboxylate

HRID 2375237Notes

Reaction equation

HRID 2375237 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([NH:26][O:27]CC4C=CC=CC=4)=[O:25])=[CH:20][CH:19]=3)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1>[Pd].CO.C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15]([O:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]([NH:26][OH:27])=[O:25])=[CH:22][CH:23]=3)=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 586118514-{[(Benzyloxy)amino]carbonyl}phenyl 1-(4-methoxyphenyl)cyclohexanecarboxylate

Product 1

HCID 98422614-[(Hydroxyamino)carbonyl]phenyl 1-(4-methoxyphenyl)-cyclohexanecarboxylateYield 64%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-{[(benzyloxy)amino]carbonyl]phenyl 1-(4-methoxyphenyl) cyclohexanecarboxylate (22a) (0.072 g, 0.16 mmol) and 5% palladium on activated carbon (0.054 g) in methanol (1 ml) was hydrogenated at room temperature until the starting material disappeared (ca. 45 minutes). The black suspension was filtered, the catalyst was washed with methanol (3×1 ml), and the filtrate was evaporated to give a white solid. The solid was suspended in diethyl ether (3 ml) and the mixture was intensively stirred overnight. The solid was filtered, washed with diethyl ether (1 ml), and dried in vacuum to give the title compound (0.037 g, 64%) as white crystals, m.p. 127-129° C. 1H NMR (DMSO-d6, HMDSO) δ: 1.18-1.90 (8H, m); 2.36-2.65 (2H, m, overlapped with a signal of DMSO); 3.76 (3H, s); 6.97 (2H, d, J=8.6 Hz); 7.01 (2H, d, J=8.8 Hz); 7.40 (2H, d, J=8.8 Hz); 7.77 (2H, d, J=8.6 Hz); 9.07 (1H, br s); 11.23 (1H, br s). HPLC analysis on Symmetry C8 column: impurities 2.2% (column size 3.9×150 mm; mobile phase acetonitrile−0.1M phosphate buffer (pH 2.5), 60:40; detector UV 230 nm; sample concentration 0.3 mg/ml; flow rate 1.0 ml/min). Anal. Calcd for C21H23NO5*0.3H2O, %: C, 67.29; H, 6.35,; N, 3.74. Found, %: C, 67.29; H, 6.23; N, 3.76.

Workup

  1. customwas hydrogenated at room temperature until the starting material
  2. custom(ca. 45 minutes)
  3. filtrationThe black suspension was filtered
  4. washthe catalyst was washed with methanol (3×1 ml)
  5. customthe filtrate was evaporated
  6. customto give a white solid
  7. filtrationThe solid was filtered
  8. washwashed with diethyl ether (1 ml)
  9. customdried in vacuum

Sources & evidence

ORD record
ord-c0727da5c73748a1a6b225fa2ba71deb
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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