3-Fluorobenzaldehyde → HCID 66960724, compound

HRID 1446493Notes

Reaction equation

HRID 1446493 reaction equation
[C:1]([O:5][C:6](=[O:26])/[C:7](=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]2)=[C:14]([O:24][CH3:25])[CH:13]=1)/[CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH:31]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(O)(=O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:26])/[C:7](=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]2)=[C:14]([O:24][CH3:25])[CH:13]=1)/[CH2:8][CH2:9][NH:10][CH2:31][C:30]1[CH:33]=[CH:34][CH:35]=[C:28]([F:27])[CH:29]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 680093-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66960838HCID 66960838, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66960724HCID 66960724, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methylene chloride (2.0 mL) solution of (E)-4-amino-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]butyric acid tert-butyl ester (71 mg), 3-fluorobenzaldehyde (21.1 μL), acetic acid (0.1 mL) and sodium triacetoxy borohydride (63.3 mg) were added one by one. After agitating reaction solution at room temperature for 5.5 hours, a saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by NH silica gel chromatography (elution solvent:ethyl acetate→ethyl acetate:ethanol=20:1), and 47.5 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customreaction solution at room temperature for 5.5 hours
  2. customthe organic layer was partitioned
  3. washAfter the obtained organic layer was washed with a saturated saline solution, it
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by NH silica gel chromatography (elution solvent:ethyl acetate→ethyl acetate:ethanol=20:1)

Sources & evidence

ORD record
ord-60233c0073b04aadb2e6fcf040da311e
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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