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

HRID 1911553ノート

反応式

HRID 1911553 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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)+.).

後処理

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

出典と根拠

ORDレコード
ord-bbfcad8f3d8e42429be36e7f4a417e92
出典データセット
uspto-grants-2013_12
特許番号
US08604061B2

反応ノート

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