Diisopropylethylamine → 3-{4-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoylamino}-propionic acid methyl ester

HRID 1669292Notes

Reaction equation

HRID 1669292 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[CH2:17][CH3:18])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.[CH3:65][O:66][C:67](=[O:71])[CH2:68][CH2:69][NH2:70].C(N(C(C)C)C(C)C)C>CN(C)C=O.C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC>[CH3:65][O:66][C:67](=[O:71])[CH2:68][CH2:69][NH:70][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([O:19][CH:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:30])([F:29])[F:1])=[CH:4][CH:5]=3)=[CH:10][CH:11]=2)[CH2:17][CH3:18])=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 673415704-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoic acid

Product 1

HCID 673430863-{4-[1-(4'-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoylamino}-propionic acid methyl esterYield 60%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-[1-(4′-Trifluoromethyl-biphenyl-4-ylmethyl)-propoxy]-benzoic acid (0.018 g, 0.04 mmol), PyBOP (0.027 g, 0.05 mmol), 3-amino-propionic acid methyl ester hydrochloride (0.011 g, 0.08 mmol), and ethyl-diisopropyl-amine (0.03 mL, 0.18 mmol) are dissolved in N,N-dimethyl-formamide (1 mL) and stirred for sixteen hours. The mixture is diluted with ethyl acetate, washed with water two times then brine. Organic layers are dried over sodium sulfate, filtered and concentrated under reduced pressure. Column chromatography on silica gel with 0-70% ethyl acetate/hexane gradient affords 0.012 g (0.02 mmol, 60%) of title compound.

Workup

  1. washwashed with water two times
  2. dry with materialOrganic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a9d4e8196f6f47d6b985d69df99273bb
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

Loading…