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

HRID 133335
Notes
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Reaction equation

HRID 133335 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dbb39c10f2294265bc30972b71f00007
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07390801B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes