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

HRID 350748Notes

Reaction equation

HRID 350748 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8a7bf08966cf4ebcbefe21111efcb4a8
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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