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

HRID 411440

반응식

HRID 411440 반응식
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]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 2829263-Chloro-4-iodoanilineHCID 522337Isobutyl 2-bromopropionateHCID 22592440tert-Butyl (3-chloro-4-iodophenyl)carbamate2회

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-eb7f75f79fab4356ba3a1068aac8122b
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559141B2

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