Methanol → HCID 59226580, compound

HRID 2192633Notes

Reaction equation

HRID 2192633 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]([OH:20])=[O:19])=[N:6][C:7]=1[C:8]1[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH:9]=1.[CH3:21]CN=C=NCCCN(C)C.Cl.CO>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:18]([O:20][CH3:21])=[O:19])=[N:6][C:7]=1[C:8]1[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH:9]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59226540HCID 59226540, compound

Product 1

HCID 59226580HCID 59226580, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-fluoro-6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)picolinic acid (1.0 equiv.) in DCM (0.3 M) was added EDC-HCl (1.0 equiv.), DMAP (1.0 equiv.), and MeOH (10 equiv.). The reaction mixture was allowed to stir at room temperature for 5 days, then diluted with ethyl acetate, washed with water, brine, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography eluting with 25-50% ethyl acetate in hexanes to yield methyl 5-fluoro-6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)picolinate as the desired product in 35% yield. LC/MS=294.2 (M+H), Rt=0.79 min.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel column chromatography
  6. washeluting with 25-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-fb1fc870bb1b4572ae93abb368cd8008
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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