Triethylamine → HCID 68898040, compound

HRID 1984560Notes

Reaction equation

HRID 1984560 reaction equation
[OH:1][C:2]([C:10](=[O:28])[NH:11][C@@H:12]1[C:18](=[O:19])[NH:17][C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[C:14]2[CH:24]=[CH:25][CH:26]=[CH:27][C:13]1=2)([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=O.[F:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([F:38])[CH:37]=1)[CH2:33]N.C([N:41](CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[F:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([F:38])[CH:37]=1)[CH2:33][N:11]([C@@H:12]1[C:18](=[O:19])[NH:17][C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[C:14]2[CH:24]=[CH:25][CH:26]=[CH:27][C:13]1=2)[C:10](=[O:28])[C:2]([OH:1])([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([NH2:41])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1452113,5-DifluorobenzylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57713978HCID 57713978, compound

Product 1

HCID 68898040HCID 68898040, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 50.0 mg (0.13 mmol) 2-hydroxy-4-methyl-2-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-ylcarbamoyl)-pentanoic acid and 37.4 mg (0.26 mmol) 3,5-difluorobenzylamine in 1.5 ml dimethylformamid were cooled to 0° C. and 20 μl (0.14 mmol) triethylamine and 54.5 mg (0.14 mmol) O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) were added. Stirring was continued overnight at room temperature. Removal of the solvent by distillation and chromatography on silicagel with heptane/ethylacetate (gradient 19:1 to 1:1) yielded 10.0 mg (15%) (R/S)-N-(3,5-difluoro-benzyl)-2-hydroxy-2-isobutyl-N-((S)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-malonamide, MS (m/e): 508.5 (M+H)+.

Workup

  1. customRemoval of the solvent
  2. distillationby distillation and chromatography on silicagel with heptane/ethylacetate (gradient 19:1 to 1:1)

Sources & evidence

ORD record
ord-ba160318a9c648829753fa46895cec42
Source dataset
uspto-grants-2009_06
Patent number
US07544679B2

Reaction notes

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