Ammonia → HCID 53877449, compound

HRID 581693Notes

Reaction equation

HRID 581693 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:16](=[O:18])[NH2:17])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH:26]1([CH2:32]Br)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.N>CO.C>[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:32][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[C:11]([C:16](=[O:18])[NH2:17])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 10796Cesium carbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 53670432HCID 53670432, compound

Product 1

HCID 53877449HCID 53877449, compound

Reagents, catalysts & solvents 2

HCID 297MethaneSolventHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (3-Carbamoyl-4-hydroxy-benzyl)-carbamic acid tert-butyl ester (2.0 g, 7.5 mmol) in 15 mL methanol at room temperature was added cesium carbonate (2.7 g, 8.3 mmol). The reaction was stirred overnight. The reaction was then concentrated under reduced pressure. N,N-dimethylformamide (50 mL) was then added, and the reaction was then reconcentrated under reduced pressure to remove any remaining methanol. The residue was then suspended in N,N-dimethylformamide (15 mL) and cyclohexylmethyl bromide (1.1 mL, 8.3 mmol) was then added, and the reaction was heated at 65° C. for 4 hours. The reaction was then concentrated under reduced pressure. The residue was diluted with ethyl acetate and 5% citric acid. The organic layer was washed with 5% citric acid (2×50 mL), 1N sodium hydroxide (2×50 mL), 5% citric acid (2×50 mL), and saturated sodium chloride (1×50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a pale yellow powder. The powder was collected and washed with ether, followed by drying under reduced pressure to yield (1.5 g, 57%). 1H NMR (400 MHz, DMSO): δ 7.68 (bs, 1H), 7.52 (d, 2H), 7.36 (t, 1H), 7.27 (d, 2H), 7.05 (d, 1H), 4.04 (d, 2H), 3.88 (d, 2H), 1.76-1.61 (m, 6H), 1.36 (s, 9H), 1.28-1.02 (m, 5H); Mass Spectrum (Chemical Ionization, 1% NH3 in CH4) m/z 363 (M+H).

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. additionN,N-dimethylformamide (50 mL) was then added
  3. customto remove any remaining methanol
  4. concentrationThe reaction was then concentrated under reduced pressure
  5. additionThe residue was diluted with ethyl acetate and 5% citric acid
  6. washThe organic layer was washed with 5% citric acid (2×50 mL), 1N sodium hydroxide (2×50 mL), 5% citric acid (2×50 mL), and saturated sodium chloride (1×50 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield a pale yellow powder
  11. customThe powder was collected
  12. washwashed with ether
  13. customby drying under reduced pressure
  14. customto yield (1.5 g, 57%)

Sources & evidence

ORD record
ord-e362b03814d44304bba07d144bf2c88b
Source dataset
uspto-grants-1999_07
Patent number
US05922697

Reaction notes

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