Potassium Carbonate → (S)-4'-(3-Amino-2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-3-oxopropyl)biphenyl-3-yl methanesulfonate

HRID 216935

Reaktionsgleichung

Reaktionsgleichung von HRID 216935
[NH2:1][C:2](=[O:29])[C@@H:3]([NH:12][C:13]([C:15]1([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH3:30][S:31]([O:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1)(=[O:33])=[O:32].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[CH3:30][S:31]([O:34][C:35]1[CH:36]=[C:37]([C:8]2[CH:9]=[CH:10][C:5]([CH2:4][C@H:3]([NH:12][C:13]([C:15]3([NH:21][C:22]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:28])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[O:14])[C:2]([NH2:1])=[O:29])=[CH:6][CH:7]=2)[CH:38]=[CH:39][CH:40]=1)(=[O:33])=[O:32]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 595685463-(Methylsulfonyloxy)phenylboronic acidHCID 59568595(S)-tert-Butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

Produkt 1

HCID 59568622(S)-4'-(3-Amino-2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-carboxamido)-3-oxopropyl)biphenyl-3-yl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

(S)-tert-butyl 4-(1-amino-3-(4-iodophenyl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iii), 300 mg), 3-(methylsulfonyloxy)phenylboronic acid (Example 12, step (i), 125 mg) and potassium carbonate (240 mg) in acetonitrile (10 mL) and water (5 mL) were stirred and heated at 90° C. under a nitrogen atmosphere with 1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride (11 mg). After 20 h the reaction was complete and the solvents were removed under reduced pressure. The residue was partitioned between water (100 mL) and ethyl acetate (100 mL), and the organic phase collected and dried over magnesium sulfate. The extract was concentrated to a gum and the crude material purified by chromatography on silica eluting with ethyl acetate to afford the sub-titled is compound (120 mg).

Aufarbeitung

  1. customthe solvents were removed under reduced pressure
  2. customThe residue was partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. customthe organic phase collected
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe extract was concentrated to a gum
  6. customthe crude material purified by chromatography on silica eluting with ethyl acetate
  7. customto afford the

Quellen und Nachweise

ORD-Eintrag
ord-e76ff5577a834b8eb64319a8d913417a
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193239B2

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