Hydrochloric Acid → HCID 58477049, compound

HRID 1258124Notes

Reaction equation

HRID 1258124 reaction equation
[CH3:1][C@:2]1([NH:19]C(=O)OC(C)(C)C)[CH2:6][CH2:5][C@@H:4]([CH2:7][C:8]2[N:12]=[C:11]([C:13](F)(F)F)[O:10][N:9]=2)[C:3]1([CH3:18])[CH3:17].N1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(C(Cl)=O)CCCCC1.Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:13]1([C:11]2[O:10][N:9]=[C:8]([CH2:7][C@@H:4]3[CH2:5][CH2:6][C@:2]([CH3:1])([NH2:19])[C:3]3([CH3:17])[CH3:18])[N:12]=2)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 75938Cyclohexanecarbonyl chlorideHCID 57518676HCID 57518676, compound

Product 1

HCID 58477049HCID 58477049, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

To a solution of tert-butyl {(1S,3S)-3-[(2Z)-2-amino-2-(hydroxyimino)ethyl]-1,2,2-trimethylcyclopentyl}carbamate (prepared in Step-1 example 56)(0.3 g, 1 mmol) in toluene, pyridine (0.079 g, 1 mmol) and cyclohexanecarbonylchloride was added and stirred for 3 hours. The reaction mixture was refluxed for another 12 h. The reaction mixture diluted with ethyl acetate, washed with 0.1N HCl. Ethyl acetate layer was separated, dried and concentrated, residue purified by silica column chromatography using 20% ethyl acetate in hexane. m/z (M+1)−100: 292.1. The product that obtained was dissolved in ethyl acetate. To this a solution of saturated HCl in ethyl acetate (2 mL) was added and reaction mixture was stirred at room temperature for two hours. The volatiles were removed under reduced pressure and triturated with hexane to afford the desired product. 1H NMR (400 MHz, d6-DMSO) δ ppm: 0.8 (s, 3H), 0.9 (s, 3H), 1.2 (s, 3H), 1.42-1.50 (m, 3H), 1.52-1.72 (m, 2H), 1.89-1.92 (m, 5H), 1.95-1.98 (m, 3H), 2.13-2.15 (m, 1H), 2.51-2.54 (m, 1H), 2.74 (m, 1H), 3.02 (m, 1H), 7.95 (bs, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for another 12 h
  2. washwashed with 0.1N HCl
  3. customEthyl acetate layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customresidue purified by silica column chromatography
  7. customThe product that obtained
  8. customreaction mixture
  9. stirringwas stirred at room temperature for two hours
  10. customThe volatiles were removed under reduced pressure
  11. customtriturated with hexane

Sources & evidence

ORD record
ord-1a949622eb704fce92195a79d47ef3ea
Source dataset
uspto-grants-2013_06
Patent number
US08466145B2

Reaction notes

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