Dichloromethane → HCID 10022833, compound

HRID 2375239Notes

Reaction equation

HRID 2375239 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:32]=[CH:31][C:8]([O:9][C:10]([C:12]2([C:18]3[CH:30]=[CH:29][C:21]([C:22]([O:24]C(C)(C)C)=[O:23])=[CH:20][CH:19]=3)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])=[CH:7][CH:6]=1)=[O:4].ClCCl.FC(F)(F)C(O)=O>C(OCC)(=O)C>[OH:1][NH:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]([C:12]2([C:18]3[CH:19]=[CH:20][C:21]([C:22]([OH:24])=[O:23])=[CH:29][CH:30]=3)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)=[O:11])=[CH:31][CH:32]=1)=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 10003308HCID 10003308, compound

Product 1

HCID 10022833HCID 10022833, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-[1-({4-[(hydroxyamino)carbonyl]phenoxy}-carbonyl)cyclohexyl]-benzoate (PX118926) (0.12 g, 0.27 mmol), dichloromethane (4 ml), and trifluoroacetic acid (1 ml) was stirred under argon atmosphere at room temperature until the starting material disappeared (ca. 2 hours). The mixture was supplemented with ethyl acetate (150 ml), the obtained solution was washed successively with water (2×100 ml), brine (50 ml), and dried (Na2SO4). The solvents were evaporated and the residue was chromatographed on silica gel with chloroform-isopropanol (9:1) as eluent to give the title compound in 48% yield as crystals, m.p. 169-170° C. 1H NMR (DMSO-d6, HMDSO) δ: 1.18-2.05 (8H, m); 2.34-2.69 (2H, m, overlapped with a signal of DMSO); 7.05 (2H, d, J=8.5 Hz); 7.62 (2H, d, J=8.4 Hz); 7.78 (2H, d, J=8.5 Hz); 7.99 (2H, d, J=8.4 Hz); 9.09 (1H, br s); 11.26 (1H, br s). HPLC analysis on Chromasil 100 C18 column: impurities 5% (column size 4.6×150 mm; mobile phase acetonitrile−0.1M phosphate buffer (pH 2.5), 60:40; detector UV 254 nm; sample concentration 1.0 mg/ml; flow rate 1.5 ml/min). Anal. Calcd for C21H21NO6*0.25H2O, %: C, 65.02; H, 5.59; N, 3.61. Found, %: C, 64.88; H, 5.49; N, 3.45.

Workup

  1. custom(ca. 2 hours)
  2. washthe obtained solution was washed successively with water (2×100 ml), brine (50 ml)
  3. dry with materialdried (Na2SO4)
  4. customThe solvents were evaporated
  5. customthe residue was chromatographed on silica gel with chloroform-isopropanol (9:1) as eluent

Sources & evidence

ORD record
ord-14969684a4d54ee6aded947f1540c0ed
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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