Acetic Acid → HCID 69048206, compound

HRID 2383497Notes

Reaction equation

HRID 2383497 reaction equation
[C:1]([O:5][C:6](=[O:26])[N:7]([C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:23]([O-:25])=[O:24])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:27][C:28]([CH3:30])=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[C:1]([O:5][C:6](=[O:26])[N:7]([C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH:28]([CH3:30])[CH3:27])[CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:23]([O-:25])=[O:24])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 69049437HCID 69049437, compound

Product 1

HCID 69048206HCID 69048206, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 14.4 g of N-(5-(3-aminophenoxy)-2-nitrophenyl)-N-methylcarbamic acid t-butyl ester, 2.90 g of acetone, 3.00 g of acetic acid, 10.6 g of sodium triacetoxyborohydride and 200 ml of anhydrous tetrahydrofuran was stirred at room temperature for 4 days. The reaction mixture was concentrated, followed by addition of water and extraction with ethyl acetate. After the extraction solution was dried over anhydrous sodium sulfate, the solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane=2/3) to give N-(5-(3-isopropylamino-phenoxy)-2-nitrophenyl)-N-methylcarbamic acid t-butyl ester, as an intermediate. This intermediate was dissolved in 200 ml of methanol, followed by addition of 2.02 g of 10% palladium-carbon, and the mixture was vigorously stirred under a hydrogen atmosphere at room temperature for 2.5 hours. After completion of the reaction, the catalyst was filtered, and the solvent was distilled off to give the title compound (12.0 g, 81% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionfollowed by addition of water and extraction with ethyl acetate
  3. dry with materialAfter the extraction solution was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customthe resulting residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate/n-hexane=2/3)

Sources & evidence

ORD record
ord-ff956fd844c34d899b05c33696d86bc4
Source dataset
uspto-grants-2012_09
Patent number
US08263631B2

Reaction notes

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