Thiazolidine → HCID 11152021, compound

HRID 1297249Notes

Reaction equation

HRID 1297249 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]([OH:23])[CH2:19][C:20]([OH:22])=O)=[CH:12][CH:11]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[S:54]1[CH2:58][CH2:57][NH:56][CH2:55]1>CN(C)C=O>[C:10]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH:18]([OH:23])[CH2:19][C:20]([N:56]2[CH2:57][CH2:58][S:54][CH2:55]2)=[O:22])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 10444ThiazolidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11391583HCID 11391583, compound

Product 1

HCID 11152021HCID 11152021, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (32 μL, 0.19 mmol) was added to a stirred solution of 5-biphenyl-4-yl-3-hydroxy-pentanoic acid (Example 1, 25 mg, 93 μmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (70 mg, 0.19 mmol) in dimethylformamide (1 mL) at room temperature under nitrogen. After stirring for 5 minutes, thiazolidine (11 μL, 0.14 mmol) was added then stirring was continued for a further 2 hours. The volatiles were removed by evaporation under reduced pressure and the residue partitioned between dichloromethane (5 mL) and water (5 mL). The phases were separated and the organic phase evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (1:1 ethyl acetate: 40–60 petroleum ether) to give the title compound (15 mg, 47%) as a white solid. LC/MS: 3.22 min; z/e 342, calcd (M+1) 342.

Workup

  1. stirringthen stirring
  2. waitwas continued for a further 2 hours
  3. customThe volatiles were removed by evaporation under reduced pressure
  4. customthe residue partitioned between dichloromethane (5 mL) and water (5 mL)
  5. customThe phases were separated
  6. customthe organic phase evaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (1:1 ethyl acetate: 40–60 petroleum ether)

Sources & evidence

ORD record
ord-869c8d205e0e4a3eba20182d91b8bff9
Source dataset
uspto-grants-2007_07
Patent number
US07250439B2

Reaction notes

Loading…