Diisopropylethylamine → HCID 74059718, compound

HRID 2306629Notes

Reaction equation

HRID 2306629 reaction equation
C(N(CC)C(C)C)(C)C.[CH2:10]([O:12][P:13]([O:27][CH2:28][CH3:29])([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]([OH:26])=O)=[CH:18][CH:17]=1)=[O:14])[CH3:11].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:54][CH2:55][C@@H:56]1[O:60][C:59](=[O:61])[N:58]([C:62]2[CH:67]=[CH:66][C:65]([C:68]3[S:69][CH2:70][C:71](=[O:74])[NH:72][N:73]=3)=[C:64]([F:75])[CH:63]=2)[CH2:57]1>CN(C=O)C>[F:75][C:64]1[CH:63]=[C:62]([N:58]2[CH2:57][CH:56]([CH2:55][NH:54][C:24]([CH:23]=[CH:22][C:19]3[CH:18]=[CH:17][C:16]([O:15][P:13](=[O:14])([O:12][CH2:10][CH3:11])[O:27][CH2:28][CH3:29])=[CH:21][CH:20]=3)=[O:26])[O:60][C:59]2=[O:61])[CH:67]=[CH:66][C:65]=1[C:68]1[S:69][CH2:70][C:71](=[O:74])[NH:72][N:73]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23528997HCID 23528997, compoundHCID 69862837HCID 69862837, compound

Product 1

HCID 74059718HCID 74059718, compoundYield 539.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (0.507 ml, 2.91 mmol) was added to 3-[4-(diethoxy-phosphoryloxy)phenyl]acrylic acid (0.065 g, 0.217 mmol) [prepared according to the procedure described in Tetrahedron Lett 1996, 37, 3635] and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.124 g 0.326 mmol) in DMF (3 ml) and stirred for 20 minutes at room temperature. 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-4H-[1,3,4]thiadiazin-5-one (0.084 g, 0.259 mmol) was added and stirring continued at room temperature overnight. The reaction mixture was partially evaporated under vacuum, diluted with water (5 ml), and extracted with ethyl acetate (50 ml). The extract was washed with brine, dried (MgSO4), and evaporated. The residue was purified by PTLC (5% MeOH/DCM) to give pure product as a white solid (0.71 g, 54%); MS (m/z): [M+H]+=607.

Workup

  1. customprepared
  2. stirringstirring
  3. waitcontinued at room temperature overnight
  4. customThe reaction mixture was partially evaporated under vacuum
  5. additiondiluted with water (5 ml)
  6. extractionextracted with ethyl acetate (50 ml)
  7. washThe extract was washed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was purified by PTLC (5% MeOH/DCM)

Sources & evidence

ORD record
ord-3160e4bbed484ea985fbc742c53327b3
Source dataset
uspto-grants-2004_12
Patent number
US06828317B2

Reaction notes

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