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

HRID 1628447ノート

反応式

HRID 1628447 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 86632868Methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoate収率 100.7%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-b3145a0841014183a88aeb0ffa2b3408
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

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