Acetic Acid → HCID 67440071, compound

HRID 1664825Notes

Reaction equation

HRID 1664825 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[NH2:13][CH2:14][CH:15]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=1[F:31])[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[F:31][C:25]1[C:26]([F:30])=[CH:27][CH:28]=[CH:29][C:24]=1[CH:15]([CH2:14][NH:13][CH2:5][C:4]1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[CH:10][C:3]=1[O:2][CH3:1])[CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 691752,4-DimethoxybenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67440237HCID 67440237, compound

Product 1

HCID 67440071HCID 67440071, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

2,4-Dimethoxybenzaldehyde was added to a solution of ethyl 6-amino-5-(2,3-difluorophenyl)hexanoate (4.73 g, 17.5 mmol) in methanol (75 mL). Acetic acid was added until the pH of the reaction mixture reached pH 5. After 30 min, sodium cyanoborohydride (1.69 g, 26.9 mmol) was added. After 1 h, the mixture was diluted with ethyl acetate and saturated aqueous sodium carbonate. The mixture was extracted with ethyl acetate and the organic extracts were washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane→95% dichloromethane/(10% ammonium hydroxide/methanol)] gave the title compound (7.3 g). MS 422.1 (M+1).

Workup

  1. waitAfter 1 h
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic extracts were washed with water, saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography [100% dichloromethane→95% dichloromethane/(10% ammonium hydroxide/methanol)]

Sources & evidence

ORD record
ord-4fbf8a1012074465bb28dd629ea8e776
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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