Hydrochloric Acid → N-{4'-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-hydroxylamine

HRID 724457

반응식

HRID 724457 반응식
Cl.[CH3:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[N:5][C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]=[N:31][OH:32])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1.C([BH3-])#N.[Na+].[OH-].[Na+]>O.O1CCCC1.CO>[CH3:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:16])([F:15])[F:17])=[CH:10][CH:9]=2)=[N:5][C:4]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][NH:31][OH:32])=[CH:26][CH:25]=2)=[CH:20][CH:19]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 73851960HCID 73851960, 화합물

생성물 1

HCID 21880682N-{4'-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-ylmethyl}-hydroxylamine수율 80.1%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Hydrochloric acid (4 N, in dioxane, 10 mL) was added dropwise into a mixture of 4′-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-biphenyl-4-carbaldehyde oxime (1.5 g, 3.56 mmol), sodium cyanoborohydride (1.1 g, 17.81 mmol), methyl alcohol (100 mL), and tetrahydrofuran (100 mL). The reaction mixture was stirred for 1 hour poured into water, basified with sodium hydroxide (2 N), and extracted with ethyl acetate. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (EtOAc/MeOH 20:1) gave an off-white solid (1.21 g, 80% yield); MS m/e 424 (M+);

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography on silica gel (EtOAc/MeOH 20:1)

출처 및 근거

ORD 기록
ord-049f1361ff794a5fa48b4128e9e8bc19
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141672B2

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