Hydrochloric Acid → HCID 11106179, compound

HRID 2217765Notes

Reaction equation

HRID 2217765 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>[Cu]I.O.CN(C)C(=O)C>[C:16]1([N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 145742L-Proline

Product 1

HCID 11106179HCID 11106179, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

Step D (1): To a sealed tube flushed with nitrogen was added L-proline (3.684 g, 32.0 mmol), potassium carbonate (6.634 g, 48.0 mmol), copper (I) iodide (609 mg, 3.2 mmol), iodobenzene (3.58 mL, 32.0 mmol) and N,N-dimethylacetamide. The mixture was heated at 90° C. for 48 hours, then cooled to room temperature. Water was added, and the pH adjusted to <3 with concentrated HCl. The aqueous phase was extracted 4 times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography (0 to 100% EtOAc/hexane gradient) afforded N-phenylproline which was used directly in the next step. LC-MS (M+H)+=192. LC-MS RT (column 1)=2.230/4.00. 1H NMR (500 MHz, CDCl3): δ 10.574 (br s, 1H), 7.29-7.25 (m, 2H), 6.785 (t, J=7.5 Hz, 1H), 6.613 (d, J=8.0 Hz, 2H), 4.25 (dd, J=2.4, 8.8 Hz, 1H), 3.60 (dt, J=2.8, 8.3 Hz, 1H), 3.36 (m, 1H), 2.38-2.01 (m, 4H).

Workup

  1. customStep D (1): To a sealed tube flushed with nitrogen
  2. temperaturecooled to room temperature
  3. extractionThe aqueous phase was extracted 4 times with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-520946f43efc4299acca2c4273d24322
Source dataset
uspto-grants-2008_08
Patent number
US07408071B2

Reaction notes

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