HCID 86757409, compound → HCID 86757410, compound

HRID 1596712Notes

Reaction equation

HRID 1596712 reaction equation
[CH2:1]([N:3]([CH2:36][CH3:37])[C:4](=[O:35])/[CH:5]=[C:6](/[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:21]([F:22])=[CH:20][CH:19]=[CH:18][C:17]=2[F:23])=[C:10]([O:24][CH2:25][CH2:26][CH2:27][O:28]C2CCCCO2)[CH:9]=1)\[CH3:7])[CH3:2]>CO.Cl>[CH2:36]([N:3]([CH2:1][CH3:2])[C:4](=[O:35])/[CH:5]=[C:6](/[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[C:17]([F:23])=[CH:18][CH:19]=[CH:20][C:21]=2[F:22])=[C:10]([O:24][CH2:25][CH2:26][CH2:27][OH:28])[CH:9]=1)\[CH3:7])[CH3:37]

Participants

4

Reactant 1

HCID 86757409HCID 86757409, compound

Product 1

HCID 86757410HCID 86757410, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of N,N-diethyl (E)-3-{4-(2,6-difluorobenzyloxy)-3-[3-(tetrahydropyran-2-yloxy)-propoxy]-phenyl}-2-butenamide (3.53 g, 6.83 mmol) in methanol (72 mL) is added IN HCl (39.0 mL), and the resulting mixture is stirred for 1 hour. After this time, the solution is concentrated to 40 mL in vacuo, and the residue is extracted with EtOAc (2×75 mL). The combined organic phase is washed with water (1×100 mL) and brine (1×100 mL), dried over MgSO4, and concentrated in vacuo to yield N,N-diethyl (E)-3-[4-(2,6-difluorobenzyloxy)-3-(3-hydroxypropoxy)-phenyl]-2-butenamide.

Workup

  1. concentrationAfter this time, the solution is concentrated to 40 mL in vacuo
  2. extractionthe residue is extracted with EtOAc (2×75 mL)
  3. washThe combined organic phase is washed with water (1×100 mL) and brine (1×100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f05ae83514ad446fa7de18f441766327
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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