1,10-Phenanthroline → HCID 21071235, compound

HRID 2113068Notes

Reaction equation

HRID 2113068 reaction equation
C(OC(=O)[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])C1C=CC=CC=1.I[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1.[C:32]([O-:35])([O-])=[O:33].[K+].[K+].N1[C:51]2[C:42](=[CH:43][CH:44]=[C:45]3[C:50]=2N=CC=C3)[CH:41]=CC=1>CS(C)=O.[Cu]I.O.CCOC(C)=O>[CH2:41]([O:35][C:32]([C:11]1([NH2:10])[CH2:16][CH2:15][CH2:14][N:13]([C:20]2[CH:25]=[CH:24][C:23]([C:26]3([C:29]([OH:31])=[O:30])[CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[C:12]1=[O:17])=[O:33])[C:42]1[CH:51]=[CH:50][CH:45]=[CH:44][CH:43]=1

Participants

9

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 13556445Benzyl (2-oxopiperidin-3-yl)carbamateHCID 217064771-(4-Iodophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 21071235HCID 21071235, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Part A. To a mixture of (2-oxo-piperidin-3-yl)-carbamic acid benzyl ester (1.35 g, 5.44 mmol) and 1-(4-iodo-phenyl)-cyclopropanecarboxylic acid (1.56 g, 5.42 mmol, 1.0 eq) in DMSO (5 mL) was added K2CO3 (3.00 g, 21.73 mmol, 4.0 eq), CuI (0.52 g, 2.74 mmol, 0.5 eq), and 1,10-phenanthroline (0.50 g, 2.74 mmol, 0.5 eq) sequentially. The mixture was heated at 120° C. overnight under N2. After cooling, EtOAc and H2O was added. The mixture was filtered. The filtrate was washed with 1N NaOH. The aqueous layer was acidified with conc. HCl, and extracted with EtOAc (3×). The organics were washed with brine, dried over MgSO4, filtered, and concentrated to give crude 1-[4-(3-benzyloxycarbonyl-amino-2-oxo-piperidin-1-yl)-phenyl]-cyclopropanecarboxylic acid (0.69 g, slightly contaminated with disubstituted compound). LC/MS (ESI) 409.2 (M+H).

Workup

  1. temperatureAfter cooling
  2. filtrationThe mixture was filtered
  3. washThe filtrate was washed with 1N NaOH
  4. extractionextracted with EtOAc (3×)
  5. washThe organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-10870804bcc442fea890041807ea6e5b
Source dataset
uspto-grants-2009_04
Patent number
US07524863B2

Reaction notes

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