Formic Acid → HCID 11429637, compound

HRID 1272582Notes

Reaction equation

HRID 1272582 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C:6](=[O:29])/[CH:7]=[CH:8]/[C:9]1[C:10]([CH:26]2[CH2:28][CH2:27]2)=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:2].C(O)=O.CCN(CC)CC.C([O-])(O)=O.[Na+]>CN(C=O)C.CC(OC)(C)C.CCCCCC.CC(OC)(C)C>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH:6]([OH:29])/[CH:7]=[CH:8]/[C:9]1[C:10]([CH:26]2[CH2:28][CH2:27]2)=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:2]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 11486489HCID 11486489, compound

Product 1

HCID 11429637HCID 11429637, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolventHCID 21982663Methyl t-butylether hexaneSolvent

Procedure

A solution of (E)-5-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-oxo-pent-4-enoic-acid-ethylester (1.6 g, 3.97 mmol), Ru[(1R,2R)-p-TsNCH(C6H5)CH(C6H5)NH2]Cl(η6-p-cymene) (12.6 mg, 0.02 mmol) and a mixture of HCOOH (1.095 g, 23.8 mmol)/NEt3 (0.963 g, 9.52 mmol) is heated in DMF (6.0 ml) at 50° C. for 20 h. After that the solution is diluted with MTBE (5 ml) and neutralised with NaHCO3 (4 ml). Standard aquous work-up with NaCl solution and extraction with MTBE and removel of the solvent give the crude product. Chromatography on silica gel using a 4:1 hexane-MTBE mixture as eluent to afford of (E)-5-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3-hydroxy-pent-4-enoic-acid-ethylester.

Workup

  1. extractionStandard aquous work-up with NaCl solution and extraction with MTBE and removel of the solvent
  2. customgive the crude product

Sources & evidence

ORD record
ord-791fe12a2db1469089b104bc3f937ecf
Source dataset
uspto-grants-2007_04
Patent number
US07208623B2

Reaction notes

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