Cyclohexanecarboxaldehyde → HCID 69686445, compound

HRID 1018389Notes

Reaction equation

HRID 1018389 reaction equation
[CH2:1]([O:8][C:9](=[O:36])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17](=[O:35])[C:18](=[N:33][OH:34])[C:19](=O)[CH2:20][O:21][C:22]23[CH2:31][CH:26]4[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]4)[CH2:23]2)[CH2:29]3)[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+:41].[CH:42]1([CH:48]=O)[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>C(O)(=O)C>[CH2:1]([O:8][C:9](=[O:36])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]([C:18]2[N:33]([OH:34])[C:48]([CH:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[N:41][C:19]=2[CH2:20][O:21][C:22]23[CH2:29][CH:28]4[CH2:27][CH:26]([CH2:25][CH:24]([CH2:30]4)[CH2:23]2)[CH2:31]3)=[O:35])[CH:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 517165Ammonium AcetateHCID 178521363HCID 178521363, compound

Product 1

HCID 69686445HCID 69686445, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-[4-(adamantan-1-yloxy)-2-hydroxyimino-3-oxo-butyrylamino]-benzoic acid benzyl ester (1.16 g, 2.36 mmol), ammonium acetate (3.64 g, 47.2 mmol) and cyclohexane carboxaldehyde (0.38 ml, 3.14 mmol) in acetic acid (30 ml) was heated at 80° C. under argon for 2 h. The mixture was cooled to room temperature and concentrated to remove most of the acetic acid. The residue was dissolved in ethyl acetate (50 ml) and neutralised with sat. sodium bicarbonate. The aqueous phase was extracted with ethyl acetate (30 ml), the combined organic phases were washed with brine (50 ml), dried (MgSO4) and the solvent was evaporated. The crude product was purified by flash column chromatography (silica, DCM/MeOH 95:5) to afford yellow foam (990 mg, 72%). 1H NMR (300MHz, CDCl3) (mixture of rotamers) 13.30 and 9.12 (1H, 2×br s), 13.08 and 10.89 (1H, 2×s), 8.28 and 8.17 (1H, 2×s), 8.10-7.80 (2H, 4×d), 7.40 (6H, m), 5.38 and 5.37 (2H, 2×s), 4.97 and 4.79 (2H, 2×s), 3.27 and 2.92 (1H, 2×m), 2.20 and 2.14 (3H, 2×br s), 1.94-1.34 (22H, m).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customto remove most of the acetic acid
  4. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  5. extractionThe aqueous phase was extracted with ethyl acetate (30 ml)
  6. washthe combined organic phases were washed with brine (50 ml)
  7. dry with materialdried (MgSO4)
  8. customthe solvent was evaporated
  9. customThe crude product was purified by flash column chromatography (silica, DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-fb2943d510c34aea91e49b4dd97ebe9a
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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