Water → HCID 67151552, 화합물

HRID 1805214노트

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HRID 1805214 반응식
C(OC([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.O.FC(F)(F)C(O)=O>C(#N)C.C(OCC)(=O)C.C1COCC1>[NH2:8][CH:12]([C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)=[O:21])=[CH:17][CH:18]=1)[CH2:11][OH:10]

참가 물질

6

반응물 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67151498(RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 67151552HCID 67151552, 화합물수율 133.7%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 21939870Tetrahydrofuran ethyl acetate용매

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온도
80 °C

실험 절차

To a solution of (RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.24 g) in acetonitrile (3 ml) were added water (9 ml) and trifluoroacetic acid (0.33 ml). The mixture was heated overnight at 80° C. The mixture was then cooled to room temperature and diluted with ethyl acetate/THF (1:1). The resulting mixture was washed sequentially with 1 N aq. sodium hydroxide solution and saturated brine, the phases were then separated and the organic phase was dried over sodium sulphate and concentrated in vacuo to afford (RS)-1-[4-(1-amino-2-hydroxy-ethyl)-phenyl]-3-(4-chloro-phenyl)-urea (0.22 g, quant.) an off-white solid. MS (ISP): 291.1 ([{37Cl}M+H—OH]+), 289.1 ([{35Cl}M+H—OH]+).

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. washThe resulting mixture was washed sequentially with 1 N aq. sodium hydroxide solution and saturated brine
  3. customthe phases were then separated
  4. dry with materialthe organic phase was dried over sodium sulphate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-afa0ac61f4034c7caa071242fcf579de
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354441B2

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