Water → (R)-3-(6-Chloro-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester

HRID 2175192

반응식

HRID 2175192 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH2:12]([O:14][C:15](=[O:25])[CH2:16][C@@H:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:13].CCN(C(C)C)C(C)C.O>CN(C=O)C.CCOC(C)=O>[CH2:12]([O:14][C:15](=[O:25])[CH2:16][C@@H:17]([NH:24][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:13]

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 915086(R)-Ethyl 3-amino-3-phenylpropanoate

생성물 1

HCID 58497459(R)-3-(6-Chloro-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl ester수율 64%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

To a solution of 2,6-dichloro-3-nitro-pyridine (0.75 g, 3.58 mmol) in DMF (30 ml) were added (R)-3-amino-3-phenylpropanoic acid ethyl ester (0.83 g, 4.29 mmol) and DIPEA (1.25 ml, 7.15 mmol). The reaction mixture was stirred at 70° C. overnight after which time it was poured into water (200 ml) and EtOAc. The layers were separated and the aqueous phase was extracted once more with EtOAc. The combined organics were washed with water twice and dried (MgSO4). Filtered and concentrated to give the crude product as an orange oil which was then purified by silica gel flash column chromatography (12 g silica gel, 5% EtOAc/Hexane) to afford 0.80 g (64%) of the title compound as a orange oil which was used without further purification.

후처리

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted once more with EtOAc
  3. washThe combined organics were washed with water twice
  4. dry with materialdried (MgSO4)
  5. filtrationFiltered
  6. concentrationconcentrated
  7. customto give the crude product as an orange oil which
  8. customwas then purified by silica gel flash column chromatography (12 g silica gel, 5% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-d06c900b10ad4bcf883d0c15f0078b8d
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062056B2

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