Water → HCID 66590931, compound

HRID 1894801Notes

Reaction equation

HRID 1894801 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[O:25][C:24]([CH:26]=[CH:27][C:28]([O-:30])=[O:29])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1)[C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O1CCCC1.CO.O>C(O)(=O)C>[CH3:3][N:4]([CH2:14][C:15]1[CH:16]=[C:17]([C:21]2[O:25][C:24]([CH:26]=[CH:27][C:28]([OH:30])=[O:29])=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1)[C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 86618119HCID 86618119, compound

Product 1

HCID 66590931HCID 66590931, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

300 mg (7.5 mmol, 12 eq) of sodium hydroxide are added to a solution of 250 mg (0.63 mmol, 1 eq) of 3-(5-{3-[(methyloctanoylamino)methyl]phenyl}furan-2-yl)acrylate in 4 mL of 9/1 tetrahydrofuran/methanol. The reaction mixture is stirred for two hours at room temperature. The reaction is stopped by adding 20 ml of water and 3 ml of acetic acid and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (90/10 dichloromethane/methanol). The oil obtained is crystallized from pentane. 140 mg of 3-(5-{3-[(methyloctanoylamino)methyl]phenyl}furan-2-yl)acrylic acid are obtained. Yield=58%. m.p.=96-98° C.

Workup

  1. extractionis then extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customThe solvents are evaporated off
  4. customthe residue is then chromatographed on silica gel (90/10 dichloromethane/methanol)
  5. customThe oil obtained
  6. customis crystallized from pentane

Sources & evidence

ORD record
ord-e0a5abe789404a16980f8277d0760634
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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