Water → (S)-4-(2-Phenoxy-ethyl)-4,5-dihydro-oxazol-2-ylamine

HRID 1026101ノート

反応式

HRID 1026101 の反応式
[NH2:1][C@@H:2]([CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:20]#[C:21]Br.O>C1COCC1.C(OCC)(=O)C>[O:7]([CH2:6][CH2:5][C@H:2]1[CH2:3][O:4][C:21]([NH2:20])=[N:1]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

7

反応物 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 20677773(S)-2-Amino-4-phenoxy-butan-1-ol

生成物 1

HCID 59173125(S)-4-(2-Phenoxy-ethyl)-4,5-dihydro-oxazol-2-ylamine収率 31.1%

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-phenoxy-butan-1-ol (175 mg) and K2CO3 (200 mg) in THF (5 ml) under an argon atmosphere was added a solution of cyanogen bromide (123 mg) 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=95:5) yielded the title compound as a white solid, (62 mg, 31%); MS (ISP): 207.1 ((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-f57da75cbf684869b5bc7a97f3502796
出典データセット
uspto-grants-2014_05
特許番号
US08729113B2

反応ノート

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