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

HRID 1026101노트

반응식

HRID 1026101 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

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)+).

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-f57da75cbf684869b5bc7a97f3502796
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729113B2

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