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

HRID 350748노트

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HRID 350748 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8a7bf08966cf4ebcbefe21111efcb4a8
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183276B2

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