Acetic Acid → HCID 59497642, compound

HRID 1747395Notes

Reaction equation

HRID 1747395 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][O:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([CH3:16])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.CCOC(C)=O>[CH3:9][O:10][C:11](=[O:17])[CH2:12][CH2:13][CH:14]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH2:8])[CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 69354Methyl levulinateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59497642HCID 59497642, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1,2-phenylenediamine (3.0 g, 27.7 mmol) and levulinic acid methyl ester (2.7 mL, 21.8 mmol) in 1,2-dichloroethane (25 mL) was added sodium triacetoxyborohydride (4.6 g, 21.7 mmol) and acetic acid (1.5 mL). The mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with EtOAc (100 mL) and washed with H2O (75 mL×3). The organic layer was dried over sodium sulfate and concentrated. The resulting residue was purified by CombiFlash with 40% EtOAc in Hexane as the eluent to afford the desired 4-(2-amino-phenylamino)-pentanoic acid methyl ester (1.05 g, 22%).

Workup

  1. washwashed with H2O (75 mL×3)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe resulting residue was purified by CombiFlash with 40% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-14d747a233514426ac025b2467f3f493
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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