4-Amino-3-hydroxybutanoic acid → Methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoate

HRID 1398801노트

반응식

HRID 1398801 반응식
[NH2:1][CH2:2][CH:3]([OH:8])[CH2:4][C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH2:13](N(CC)CC)C.Cl[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][C:22]=1[N+:30]([O-:32])=[O:31]>CO.C(OCC)(=O)C.O1CCCC1>[N+:30]([C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([N+:27]([O-:29])=[O:28])[C:21]=1[NH:1][CH2:2][CH:3]([OH:8])[CH2:4][C:5]([O:7][CH3:13])=[O:6])([O-:32])=[O:31]

참가 물질

8

반응물 4

HCID 21494-Amino-3-hydroxybutanoic acidHCID 8471TriethylamineHCID 118141-Chloro-2,6-dinitrobenzeneHCID 24386Thionyl Chloride

생성물 1

HCID 86632868Methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoate

시약·촉매·용매 3

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of rac-4-amino-3-hydroxybutyric acid (2.00 g, 16.8 mmol) in methanol (40 mL) was added thionyl chloride (1.72 mL, 23.6 mmol) at 0° C. The resultant mixture was stirred at room temperature for 1 hr and concentrated in vacuo. To a mixture of the residue, triethylamine (5.85 mL, 42.0 mmol) and tetrahydrofuran (34 mL) was added 2-chloro-1,3-dinitrobenzene (1.70 g, 8.39 mmol) at room temperature. After the resultant mixture was stirred at 50° C. for 2 hr, the mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow, solid (2.53 g, 8.45 mmol, quant).

후처리

  1. concentrationconcentrated in vacuo
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-7a4b91fff81647bfa2f82d3480c797ab
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901141B2

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