Bis(2-pyridyl) ketone → 2-Heptenoic acid

HRID 1604068Notes

Reaction equation

HRID 1604068 reaction equation
C1(CCCCNC(C2N=C(C3C=CC(/[C:25](/C4C=NC=CC=4)=[CH:26]\[CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=CC=3)OC=2)=O)CCCCC1.N1C=CC=CC=1C(C1C=CC=CN=1)=O.[Br-].C(CCCCC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(O)=O.CC([O-])(C)C.[K+]>C1COCC1.CO>[C:31]([OH:33])(=[O:32])/[CH:30]=[CH:29]/[CH2:28][CH2:27][CH2:26][CH3:25]

Participants

7

Reactant 4

HCID 88065Bis(2-pyridyl) ketoneHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 9958626HCID 9958626, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 52827092-Heptenoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(Alternative preparation of Example 2)-G: (E)-7-[4-[4-[[(4 -Cyclohexylbutyl)amino]carbonyl]-2-oxazolyl]phenyl]-7-(3-pyridyl)hept-6-enoic Acid: Prepared as above from 0.952 g (2.2 mmol) of the pyridyl ketone, 2.00 g (4.4 mmol) of (5-carboxy-pentyl)triphenylphosphonium bromide, and 8.8 mL (8.8 mmol) of 1.0 M t-BuOK in 6.0 mL of THF at 0° C. for 2 h. Preparative HPLC with MeOH--AcOH--CH2Cl2 (2:1:97) furnished total amount of 1.06 g (90%) of the (E)- and (Z)-product (E/Z=8.7:1) from which 941.8 mg of (E)-heptenoic acid was separated cleanly: mp 52-56° C.; 1H NMR (CDCl3) δ8.55 (br s, 1H), 8.47 (d, J=2.7 Hz, 1H), 8.27 (s, 1H), 8.04 (d, J=8.2 Hz, 2H), 7.47 (d, J=8.0 Hz, 1H), 7.26 (d, J=8.2 Hz, 2H), 7.33 (buried, 1H), 7.12 (t, J=5.9 Hz, 1H), 6.18 (t, J=7.5 Hz, 1H), 3.43 (ddd, J=6.9, 6.8, 6.6 Hz, 2H), 2.31 (dd J=7.2, 6.9 Hz, 2H), 2.19 (ddd, J=7.3, 7.2, 7.1 Hz, 2H), 1.68-0.82 (m, 21H); FDMS 530 (M+1). Anal. (C32H39N3O4.0.2 C2H4O2) C, H, N.

Sources & evidence

ORD record
ord-91604294ea3d4a27ac5f92bcb68823b9
Source dataset
uspto-grants-1999_11
Patent number
US05990308

Reaction notes

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