Potassium Carbonate → HCID 72551667, compound

HRID 749027Notes

Reaction equation

HRID 749027 reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].[C:16]([NH:23][C@H:24]([C:33]([OH:35])=[O:34])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CN(C=O)C.O>[C:19]([O:18][C:16]([NH:23][CH:24]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=[O:11])=[CH:28][CH:27]=1)[C:33]([OH:35])=[O:34])=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

Product 1

HCID 72551667HCID 72551667, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Potassium carbonate (7.36 g, 53.31 mmol) and -2-fluorobenzaldehyde (9.3 mL, 88.85 mmol) were added to a solution of Boc-tyrosine (5.0 g, 17.77 mmol) in anhydrous DMF (20 mL). The resulting suspension was refluxed at 75±5° C. under an atmosphere of argon. After 48 hr, the reaction mixture was cooled to room temperature, diluted with water (100 mL) and extracted with EtOAc (2×50.0 mL). The aqueous layer was collected, acidified with 5.0 M HCl to pH ˜2.0 and extracted with EtOAc (2×100 mL). The resulting EtOAc layer was extracted with water (1×100 mL) and brine (1×100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to yield the desired aldehyde, 58, as a low melting solid (6.4 g, ˜99%). 1H NMR (400 MHz, DMSO-d6): 12.62(s, 1H), 10.38 (s, 1H), 7.84 (dd, J=8.0 and 2.0 Hz, 1H), 7.64 (dt, J=7.2 and 1.6 Hz, 1H) 7.31 (d, J=8.8 Hz, 1H), 7.27 (t, J=7.6 Hz, 2 Hz), 7.13 (d, J=8.4 Hz, 1H), 7.06 (d, J=8.4 Hz, 2H) 6.89 (d, J=8.4 Hz, 1H), 4.09 (ddd, J=12.8, 10.8 and 4.4 Hz, 1H), 3.02 (dd, J=13.6 and 4.4 Hz, 1H), 2.81 (dd, J=13.6 and 10.4 Hz, 1H) 1.32 (s, 9H).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×50.0 mL)
  3. customThe aqueous layer was collected
  4. extractionextracted with EtOAc (2×100 mL)
  5. extractionThe resulting EtOAc layer was extracted with water (1×100 mL) and brine (1×100 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f35bfc67f1e43fb9473ff976967aed9
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

Loading…