Triethylamine → 3-(3-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoylamino)-propionic acid methyl ester

HRID 1669325Notes

Reaction equation

HRID 1669325 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([C:19]1[CH:20]=[N:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5](O)=[O:6].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.[CH3:69][O:70][C:71](=[O:75])[CH2:72][CH2:73][NH2:74].C(N(CC)CC)C>CN(C)C=O.O.C(OCC)(=O)C>[CH3:69][O:70][C:71](=[O:75])[CH2:72][CH2:73][NH:74][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([O:11][CH:12]([C:19]2[CH:20]=[N:21][C:22]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:32])[F:34])=[CH:29][CH:30]=3)=[CH:23][CH:24]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:2]([F:1])[CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 673440023-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acid

Product 1

HCID 673417153-(3-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoylamino)-propionic acid methyl esterYield 101.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 3-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acid (0.033 g, 0.07 mmol), PyBOP (0.044 g, 0.084 mmol), 3-amino-propionic acid methyl ester hydrochloride (0.0195 g, 0.14 mmol) and triethyl-amine (0.04 mL, 0.28 mmol) in N,N-dimethyl-formamide (1.5 mL). Stir for sixteen hours at room temperature. Dilute reaction with ethyl acetate and water. Wash organic layer with water two times then wash with saturated sodium chloride solution. Dry organic fraction with Na2SO4, filter and concentrate under reduced pressure. Purify on silica gel chromatography (30-80% Ethyl acetate/hexanes gradient) to provide 0.04 g of title compound (99%).

Workup

  1. additionDilute
  2. washWash organic layer with water two times then wash with saturated sodium chloride solution
  3. filtrationDry organic fraction with Na2SO4, filter
  4. concentrationconcentrate under reduced pressure
  5. customPurify on silica gel chromatography (30-80% Ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-df91db0100a547e289f125d4df2b25db
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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