Ethyl Acetate → HCID 86674692, 화합물

HRID 710276노트

반응식

HRID 710276 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O.C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][C:3]=1[Br:21]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 67240315HCID 67240315, 화합물

생성물 1

HCID 86674692HCID 86674692, 화합물수율 94.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In a 100 mL round-bottomed flask, (R)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (4.3 g, 15.4 mmol) was dissolved in dimethylformamide (30 ml). N-Bromosuccinimide (2.75 g, 15.4 mmol) was added and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into ethyl acetate and extracted with saturated sodium chloride solution. The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 100 g, gradient 0-50% ethyl acetate in heptane) to yield a white solid (5.2 g, 94%), MS (ISP): 301.3 ([{79Br}M-tBu+H]+), 303.4 ([{81Br}M-tBu+H]+).

후처리

  1. extractionextracted with saturated sodium chloride solution
  2. dry with materialThe organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by flash chromatography (silica gel, 100 g, gradient 0-50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-b97fe8754bfa46f593ff24da998a6149
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181230B2

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