Boron trifluoride etherate → N,N,N',N'-tetramethyl 3,3'-(((3-(2-(4-(1-methylethyl)-2-thiazolyl)ethenyl)phenyl)methylene)bis(thio))-bispropanamide

HRID 1088487Notes

Reaction equation

HRID 1088487 reaction equation
CC(C1N=C(C=CC2C=C(C=CC=2)C=O)SC=1)C.SCCC(OC)=O.[CH3:26][N:27]([CH3:33])[C:28](=[O:32])[CH2:29][CH2:30][SH:31].B(F)(F)F.CCOCC.CC(C1N=C(C=CC2C=C(C(SCCC(OC)=O)SCCC(OC)=O)C=CC=2)SC=1)C.[CH3:74][N:75]([CH3:105])[C:76](=[O:104])[CH2:77][CH2:78][S:79][CH:80](SCCC(OC)=O)[C:81]1[CH:86]=[CH:85][CH:84]=[C:83]([CH:87]=[CH:88][C:89]2[S:90][CH:91]=[C:92]([CH:94]([CH3:96])[CH3:95])[N:93]=2)[CH:82]=1>C(Cl)Cl>[CH3:26][N:27]([CH3:33])[C:28](=[O:32])[CH2:29][CH2:30][S:31][CH:80]([C:81]1[CH:86]=[CH:85][CH:84]=[C:83]([CH:87]=[CH:88][C:89]2[S:90][CH:91]=[C:92]([CH:94]([CH3:96])[CH3:95])[N:93]=2)[CH:82]=1)[S:79][CH2:78][CH2:77][C:76]([N:75]([CH3:74])[CH3:105])=[O:104]

Participants

8

Reactant 6

HCID 8000Boron trifluoride etherateHCID 18050Methyl 3-mercaptopropionateHCID 11126302Propanamide, 3-mercapto-N,N-dimethyl-HCID 53642997Dimethyl 3,3'(((3-(2-(4-(1-methylethyl)-2-thiazolyl)ethenyl)phenyl)methylene)-bis (thio))bispropanoateHCID 540138533-(2-(4-(1-Methylethyl)-2-thiazolyl)ethenyl)benzaldehydeHCID 54570341Methyl 3-((1-((3-dimethylamino-3-oxopropyl)thio)-1-(3-(2-(4-(1-methyl-ethyl)-2-thiazolyl)ethenyl)phenyl)methyl)thio)-propanoate

Product 1

HCID 54463992N,N,N',N'-tetramethyl 3,3'-(((3-(2-(4-(1-methylethyl)-2-thiazolyl)ethenyl)phenyl)methylene)bis(thio))-bispropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the aldehyde of Step 1 (430 mg), methyl 3-mercaptopropanoate (190 μL, 1 equiv.) and N,N-dimethyl 3-mercaptopropanamide (223 mg, 1 equiv.) in CH2Cl2 (10 mL), BF3.Et2O (620 μL, 3 equiv.) is added slowly and the mixture is stirred 1.5 hours. The reaction is quenched with 25% aqueous NH4OAc at 0° C. The products are extracted with EtOAc and separated by flash chromatography on silica using a gradient of EtOAc:toluene (from 10:90 to 40:60) and acetone:toluene 1:1. Three products are obtained: first, dimethyl 3,3'(((3-(2-(4-(1-methylethyl)-2-thiazolyl)ethenyl)phenyl)methylene)-bis (thio))bispropanoate; second, methyl 3-((1-((3-dimethylamino-3-oxopropyl)thio)-1-(3-(2-(4-(1-methyl-ethyl)-2-thiazolyl)ethenyl)phenyl)methyl)thio)-propanoate; and third, the title compound.

Workup

  1. customThe reaction is quenched with 25% aqueous NH4OAc at 0° C
  2. extractionThe products are extracted with EtOAc
  3. customseparated by flash chromatography on silica using a gradient of EtOAc
  4. customThree products are obtained

Sources & evidence

ORD record
ord-f6185ce0e36c4f5eac0548a8e14ac555
Source dataset
uspto-grants-1990_10
Patent number
US04962117

Reaction notes

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