Potassium Carbonate → HCID 18338256, compound

HRID 2298261Notes

Reaction equation

HRID 2298261 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[C:9]([O:13][C:14](=[O:42])[C@H:15]([CH2:34][C:35]1[CH:40]=[CH:39][C:38](O)=[CH:37][CH:36]=1)[NH:16][C:17](=[O:33])[C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24])([CH3:12])([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[C:49]1(B(O)O)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:9]([O:13][C:14](=[O:42])[C@H:15]([CH2:34][C:35]1[CH:36]=[CH:37][C:38]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[CH:39][CH:40]=1)[NH:16][C:17](=[O:33])[C@@H:18]1[CH2:22][CH2:21][CH2:20][N:19]1[S:23]([C:26]1[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=1)(=[O:25])=[O:24])([CH3:10])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 2758875TrifluoromethanesulfonateHCID 69875142HCID 69875142, compound

Product 1

HCID 18338256HCID 18338256, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared from the corresponding triflate (which was prepared from (N-(Toluene-4-sulfonyl)-L-prolyl-L-tyrosine tert-butyl ester as taught by Tilley and coworkers, J. Org. Chem., 55, 906, 1990). The dipeptide (505 mg, 0.8 mmol.), a catalytic amount of tetrakis(triphenylhosphine)palladium(0), potassium carbonate (201 mg, 1.5 eq.), phenylboronic acid (199 mg, 2.0 eq.), and 15 mL of toluene were refluxed for 10 hours with stirring. Ethyl acetate was added and the organic layer was washed with water, 1N NaOH, brine and dried over magnesium sulfate. Upon filtration, the solvent was evaporated under reduced pressure. The crude material was purified on a preparative plate (1:1 ethyl acetate:hexanes). The silica gel was washed several times with acetonitrile and ethyl acetate. The combined fractions were evaporated and the residue was dried under reduced pressure.

Workup

  1. washthe organic layer was washed with water, 1N NaOH, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationUpon filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe crude material was purified on a preparative plate (1:1 ethyl acetate:hexanes)
  6. washThe silica gel was washed several times with acetonitrile and ethyl acetate
  7. customThe combined fractions were evaporated
  8. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-ac1c5f23ea384c70953214ede7d969de
Source dataset
uspto-grants-2002_12
Patent number
US06492421B1

Reaction notes

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