Pyridine → HCID 178501862, compound

HRID 1713829Notes

Reaction equation

HRID 1713829 reaction equation
Cl[C:2](=[O:7])[C:3]([O:5][CH3:6])=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:6][O:5][C:3](=[O:4])[C:2]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]2[CH2:16][CH2:17][C@H:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]2)=[CH:13][CH:14]=1)=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 178451142HCID 178451142, compound

Product 1

HCID 178501862HCID 178501862, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl chlorooxoacetate (2.5 g, 20.7 mmol) was added dropwise to a mixture of tert-butyl trans-4-(4-aminophenyl)cyclohexanecarboxylate (3.8 g, 13.8 mmol) and pyridine (2.2 mL, 27.6 mmol) in DCM (40 mL) at 10° C. The reaction mixture was warmed to room temperature and stirred for 16 h and then quenched with water. The layers were separated and the organic layer was washed with brine. The organic layer was dried and concentrated in vacuo and the residue was purified by chromatography, eluting with 10-50% ethyl acetate in isohexane, to give the title compound (4.0 g, 80%) as an oil; 1H NMR δ 1.4 (9H, s), 1.4-1.55 (4H, m), 1.8-1.9 (2H, m), 1.9-2.05 (2H, m), 2.2-2.3 (1H, m), 2.4-2.6 (1H, m), 3.75 (3H, s), 7.2 (2H, d), 7.65 (2H, d); MS m/e (M−H)− 360.

Workup

  1. customquenched with water
  2. customThe layers were separated
  3. washthe organic layer was washed with brine
  4. customThe organic layer was dried
  5. concentrationconcentrated in vacuo
  6. customthe residue was purified by chromatography
  7. washeluting with 10-50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-6093bc67a4d44cba8f294c13d8c8511c
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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