Benzathine → (RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1805213

반응식

HRID 1805213 반응식
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[O:31])=[CH:25][CH:24]=1.[F-].[K+].C(NCCNCC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([NH:32][C:30]([NH:29][C:26]3[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=3)=[O:31])=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 8793BenzathineHCID 87964-ChlorophenylureaHCID 522689Potassium FluorideHCID 67151644(RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 67151498(RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester수율 14%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

A stirred suspension of (RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.60 g), 4-chlorophenylurea (0.81 g), potassium fluoride (2.88 g, 40 wt % on alumina), N,N′-dibenzylethylenediamine (0.14 ml) and copper(I) iodide (0.11 g) in THF (16 ml) in a sealed tube was heated at 90° C. for 30 minutes under microwave irradiation. The mixture was then cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.24 g, 14%) as a light yellow solid. MS (ISP): 392.1 ([{37Cl}M+H—C4H8]+), 390.1 ([{35Cl}M+H—C4H8]+).

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

출처 및 근거

ORD 기록
ord-07b2e2e9e8924e7a82757d4df75d472a
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354441B2

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