Ammonium Chloride → HCID 67015503, compound

HRID 1617523Notes

Reaction equation

HRID 1617523 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=[O:33])[CH2:9][CH:10]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30](O)=[O:31])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:5]=[CH:4][N:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[CH2:57]([O:59][C:60](=[O:64])[CH2:61][CH2:62][NH2:63])[CH3:58].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O.C(N(CC)CC)C>[CH2:57]([O:59][C:60](=[O:64])[CH2:61][CH2:62][NH:63][C:30]([C:27]1[CH:26]=[CH:25][C:24]([C:21]2[CH:20]=[CH:19][C:18]([CH:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:17])[CH2:9][C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=3)=[O:33])=[CH:23][CH:22]=2)=[CH:29][CH:28]=1)=[O:31])[CH3:58]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66667194HCID 66667194, compound

Product 1

HCID 67015503HCID 67015503, compoundYield 117.3%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4′-[3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid (50 mg) in THF (1 mL) was added TBTU (41 mg) and triethylamine (0.048 mL) and the resulting mixture was stirred at room temperature for 10 min. Beta-alanine ethyl ester hydrochloride (21.2 mg) was added and the reaction mixture was stirred at rt overnight. A saturated solution of NH4Cl and EtOAc were added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to yield the title compound (72 mg) as a light yellow oil, MS (ESI+): m/z=535.3 ([M+H]+).

Workup

  1. stirringthe reaction mixture was stirred at rt overnight
  2. customthe phases were separated
  3. extractionthe inorganic one was extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56ccd5cb62e34f68874d25c7a4ce9e5f
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

Loading…