Acetic Anhydride → HCID 66778230, compound

HRID 2091204Notes

Reaction equation

HRID 2091204 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([N:26]([CH3:34])[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:25])=[CH:20][CH:19]=3)[CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:7]([CH3:35])[C:6]=2[CH:36]=1.C(N(CC)CC)C.[C:44](OC(=O)C)(=[O:46])[CH3:45].C(=O)([O-])O.[Na+]>O1CCCC1>[C:44]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([N:26]([CH3:34])[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:25])=[CH:20][CH:19]=3)[CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)=[C:7]([CH3:35])[C:6]=2[CH:36]=1)(=[O:46])[CH3:45]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 66778821HCID 66778821, compound

Product 1

HCID 66778230HCID 66778230, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (10 mL) of ethyl 3-{[(4-{[(5-amino-3-methyl-1-benzofuran-2-yl)(cyclohexyl)methyl]amino}phenyl)carbonyl](methyl)amino}-propanoate (480 mg) synthesized above in tetrahydrofuran were added triethylamine (204 μL) and acetic anhydride (138 μL), and the mixture was stirred at room temperature for 2.5 days. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (90% ethyl acetate/hexane) to give the title object compound (366 mg, 70%) as a pale-brown oil

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (90% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ef7701933b0a440e99e570fe32dc6c1a
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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