Triethylamine → 4-{3-[2-Amino-4-(4-chlorophenyl)-5-thiazolyl]propanoyl}thiomorpholine-1,1-dioxide

HRID 350748ノート

反応式

HRID 350748 の反応式
[NH2:1][C:2]1[S:3][C:4]([CH2:14][CH2:15][C:16]([OH:18])=O)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.P(C#N)(OCC)(OCC)=O.Cl.[NH:30]1[CH2:35][CH2:34][S:33](=[O:37])(=[O:36])[CH2:32][CH2:31]1.C(N(CC)CC)C>O.CN(C)C=O>[NH2:1][C:2]1[S:3][C:4]([CH2:14][CH2:15][C:16]([N:30]2[CH2:35][CH2:34][S:33](=[O:37])(=[O:36])[CH2:32][CH2:31]2)=[O:18])=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[N:6]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 12324096Thiomorpholine 1,1-dioxide hydrochlorideHCID 215636173-[2-Amino-4-(4-chlorophenyl)-5-thiazolyl]propionic acid

生成物 1

HCID 210887084-{3-[2-Amino-4-(4-chlorophenyl)-5-thiazolyl]propanoyl}thiomorpholine-1,1-dioxide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl]propionic acid (2.67 g), diethyl cyanophosphate (1.69 g), thiomorpholine-1,1-dioxide hydrochloride (1.62 g), triethylamine (2.9 ml) and N,N-dimethylformamide (40 ml) was stirred at room temperature for 3 hrs. The reaction mixture as poured into water, extracted with ethyl acetate, washed with 0.1N aqueous sodium hydroxide solution and water, dried over anhydrous magnesium sulfate and concentrated. The precipitated solid was collected by filtration to give 4-{3-[2-amino-4-(4-chlorophenyl)-5-thiazolyl]propanoyl}thiomorpholine-1,1-dioxide as a colorless powder. Recrystallization from ethanol-isopropyl ether gave colorless prism crystals. melting point: 220–222° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with 0.1N aqueous sodium hydroxide solution and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. filtrationThe precipitated solid was collected by filtration

出典と根拠

ORDレコード
ord-8a7bf08966cf4ebcbefe21111efcb4a8
出典データセット
uspto-grants-2007_02
特許番号
US07183276B2

反応ノート

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