Sodium hydride → N-BOC-N-(3-chloro-4-iodophenyl)alanine iso-butyl ester

HRID 133335

Reaktionsgleichung

Reaktionsgleichung von HRID 133335
ClC1C=C(C=CC=1I)N.[C:10]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[C:20]([Cl:25])[CH:19]=1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[H-].[Na+].Br[CH:29]([CH3:37])[C:30]([O:32][CH2:33][CH:34]([CH3:36])[CH3:35])=[O:31]>CN(C=O)C.ClCCl>[CH2:33]([O:32][C:30](=[O:31])[C@H:29]([CH3:37])[N:17]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:18]1[CH:23]=[CH:22][C:21]([I:24])=[C:20]([Cl:25])[CH:19]=1)[CH:34]([CH3:36])[CH3:35]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 2829263-Chloro-4-iodoanilineHCID 522337Isobutyl 2-bromopropionateHCID 22592440tert-Butyl (3-chloro-4-iodophenyl)carbamate2×

Produkt 1

HCID 21341411N-BOC-N-(3-chloro-4-iodophenyl)alanine iso-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Following General Procedure AR above and using 3-chloro-4-iodoaniline (Aldrich), N-BOC-3-chloro-4-iodoaniline was prepared. To a stirred slurry of 5.0 equivalents of sodium hydride in DMF was added 1.0 equivalent of N-BOC-3-chloro-4-iodoaniline and then 1.1 equivalents of iso-butyl 2-bromopropionate (from Example AD above) were slowly added. The reaction was heated to 100° C. for 10 hours, cooled, diluted with dichloromethane and washed with cold 1N HCl, water and brine. The solvents were removed at reduced pressure and the residue was chromatographed to provide N-BOC-N-(3-chloro-4-iodophenyl)alanine iso-butyl ester as a clear oil. Following General Procedure AN above, the BOC group was removed from N-BOC-N-(3-chloro-4-iodophenyl)alanine iso-butyl ester to provide the title compound. The BOC-removal reaction was monitored by tlc on silica gel (Rf=0.58 in 30% EtOAc/hexanes) and purification was by preparative plate chromatography (silica gel using 30% EtOAc/hexanes as the eluant). The compound was further purified by chromatography on an HPLC chiral column (Chiralcel OD).

Aufarbeitung

  1. customwas prepared
  2. temperaturecooled
  3. washwashed with cold 1N HCl, water and brine
  4. customThe solvents were removed at reduced pressure
  5. customthe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-dbb39c10f2294265bc30972b71f00007
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390801B2

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