Pyridine → HCID 178471537, compound

HRID 1713871Notes

Reaction equation

HRID 1713871 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]([CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[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]([CH:21]([CH3:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:19][CH2:20]2)=[CH:13][CH:14]=1)=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 178471529HCID 178471529, compound

Product 1

HCID 178471537HCID 178471537, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl chlorooxoacetate (670 mg, 5.45 mmol) in DCM (3 mL) was added in one portion to a solution of trans-ethyl 2-[4-(4-aminophenyl)cyclohexyl]propanoate (1.0 g, 3.63 mmol) and pyridine (0.59 mL, 7.26 mmol) in DCM (22 mL) at 5° C. and the mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was concentrated in vacuo and EtOAc (30 mL) was added. The layers were separated and the organic layer was washed with water (25 mL) and brine (25 mL). The organic layer was dried and concentrated in vacuo to give the title compound (1.3 g, 99%) as a solid; 1H NMR δ (CDCl3) 1.0-1.1.25 (2H, m), 1.1 (3H, d), 1.2 (3H, t), 1.3-1.47 (2H, m), 1.48-1.55 (2H, m), 1.68-1.79 (1H, m), 1.8-1.95 (2H, m), 2.18-2.28 (1H, m), 2.35-2.5 (1H, m), 3.9 (3H, t), 4.08 (2H, q), 7.12 (2H, d), 7.47 (2H, d); MS m/e (M−H)− 360.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and EtOAc (30 mL)
  2. additionwas added
  3. customThe layers were separated
  4. washthe organic layer was washed with water (25 mL) and brine (25 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea32961d35d547378e8fbc6ddd79f06b
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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