Benzenepropanoic acid → HCID 18786986, compound

HRID 1107379Notes

Reaction equation

HRID 1107379 reaction equation
[C:1]([OH:11])(=O)[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN([C:15]([O:19]N1N=NC2C1=CC=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:36]([N:39](CC)[CH:40]([CH3:42])[CH3:41])(C)[CH3:37].CN(C=[O:49])C>CCOC(C)=O>[CH3:15][O:19][C:37](=[O:49])[CH2:36][N:39]([CH:40]([CH3:42])[CH3:41])[C:1](=[O:11])[CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 107Benzenepropanoic acidHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 18786986HCID 18786986, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the hydrochloride salt prepared above (1.0 g, 5.97 mmol) and hydrocinnamic acid (0.9 g, 5.97 mmol) in DMF (20 mL) was added O-benzotriazole-N,N,N',N'-tetramethyluronium hexafluorophosphate (2.26 g, 5.97 mmol) followed by N,N-diisopropylethylamine (1.69 g, 13.1 mmol). The reaction was stirred at ambient temperature for 48 hours. The reaction mixture was diluted with 1:1 EtOAc:hexane and washed with H2O (2×), HCl (10%) saturated NaHCO3 and brine. The solution was dried (MgSO4), evaporated, and combined with an additional material obtained by the same acylation procedure. The combined batches were purified by flash chromatography on silica gel with 2:1 hexane:EtOAc as the eluent. There was obtained N-2-propyl-N-[(3-phenyl)propionyl]glycine methyl ester (2.8 g); LRMS (M+H)+ =264.0.

Workup

  1. washhexane and washed with H2O (2×), HCl (10%) saturated NaHCO3 and brine
  2. dry with materialThe solution was dried (MgSO4)
  3. customevaporated
  4. customobtained by the same acylation procedure
  5. customThe combined batches were purified by flash chromatography on silica gel with 2:1 hexane

Sources & evidence

ORD record
ord-01d7fb81dd1f4f9881311c564fe7e979
Source dataset
uspto-grants-2000_05
Patent number
US06060462

Reaction notes

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