Imidazole → Benzyl (S)-3-(Boc-amino)-4-iodobutanoate

HRID 1182092

Reaktionsgleichung

Reaktionsgleichung von HRID 1182092
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.N1C=CN=C1.[CH2:27]([O:34][C:35](=[O:48])[CH2:36][C@H:37]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:38]O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(Cl)Cl>[CH2:27]([O:34][C:35](=[O:48])[CH2:36][C@H:37]([NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:38][I:20])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 10040985Phenylmethyl (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-4-hydroxybutanoate

Produkt 1

HCID 11258642Benzyl (S)-3-(Boc-amino)-4-iodobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A suspension of polymer bound triphenyl phosphine (18.25 g, 54.76 mmol) in DCM (100 ml) is treated with iodine (12.2 g, 48.1 mmol) and the reaction mixture stirred at ambient temperature for 15 minutes. Imidazole (3.72 g, 54.7 mmol) is added and the reaction mixture stirred for a further 15 minutes. A solution of (S)-3-tert-butoxycarbonylamino-4-hydroxy-butyric acid benzyl ester (6.76 g, 21.9 mmol) in DCM (100 ml) is added. The suspension is stirred at reflux for 1.5 hours, then filtered through Celite™ filter material, washing through with DCM. The combined organic phase is washed with an aqueous solution of 10% sodium thiosulphate, water and brine, then dried over magnesium sulphate and evaporated. The crude product is chromatographed over flash silica using 8% ethylacetate in iso-hexane as eluent to afford (S)-3-tert-butoxycarbonylamino-4-iodo-butyric acid benzyl ester. [M-BOC] 320.12

Aufarbeitung

  1. additionA suspension of polymer
  2. stirringthe reaction mixture stirred for a further 15 minutes
  3. stirringThe suspension is stirred
  4. temperatureat reflux for 1.5 hours
  5. filtrationfiltered through Celite™
  6. filtrationfilter material
  7. washwashing through with DCM
  8. washThe combined organic phase is washed with an aqueous solution of 10% sodium thiosulphate, water and brine
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. customThe crude product is chromatographed over flash silica using 8% ethylacetate in iso-hexane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-03e7a4abcdd845eca11b0eb3e0bc38af
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288537B2

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