Water → (S)-4-[2-(2-Chloro-phenyl)-ethyl]-4-methyl-4,5-dihydro-oxazol-2-ylamine

HRID 1911553노트

반응식

HRID 1911553 반응식
[NH2:1][C@@:2]([CH3:14])([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:21]#[C:22]Br.O>C1COCC1.C(OCC)(=O)C>[Cl:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][C@@:2]1([CH3:14])[CH2:3][O:4][C:22]([NH2:21])=[N:1]1

참가 물질

7

반응물 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 68712118(S)-2-Amino-4-(2-chloro-phenyl)-2-methyl-butan-1-ol

생성물 1

HCID 24963280(S)-4-[2-(2-Chloro-phenyl)-ethyl]-4-methyl-4,5-dihydro-oxazol-2-ylamine수율 33%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a stirred mixture of (S)-2-amino-4-(2-chloro-phenyl)-2-methyl-butan-1-ol (0.190 g, 0.89 mmol) and K2CO3 (0.155 g, 1.12 mmol) in THF (10 ml) under an argon atmosphere was added a solution of cyanogen bromide (0.119 g, 1.12 mmol) in THF (1 ml). The mixture was stirred for 18 hours, then water and ethyl acetate were added. The organic layer was washed with water, dried over MgSO4 and evaporated over Isolute® Flash-NH2 silica gel. Chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/MeOH=90:10) yielded the title compound as off-white solid, (0.070 g, 33%); MS (ISP): 239.2; 241.2 ((M+H)+.).

후처리

  1. washThe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. customevaporated over Isolute® Flash-NH2 silica gel

출처 및 근거

ORD 기록
ord-bbfcad8f3d8e42429be36e7f4a417e92
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604061B2

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