Isatoic Anhydride → 2-(2-Amino-benzoylamino)-pentanoic acid methyl ester

HRID 388451Notes

Reaction equation

HRID 388451 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.Cl.[CH3:14][O:15][C:16](=[O:22])[CH:17]([NH2:21])[CH2:18][CH2:19][CH3:20].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH3:14][O:15][C:16](=[O:22])[CH:17]([NH:21][C:2](=[O:4])[C:1]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:6])[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 8359Isatoic AnhydrideHCID 8471TriethylamineHCID 22492254Methyl 2-aminopentanoate hydrochloride

Product 1

HCID 687288232-(2-Amino-benzoylamino)-pentanoic acid methyl esterYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of isatoic anhydride (750 mg, 4.60 mmol) and 2-amino-pentanoic acid methyl ester hydrochloride (1.4 g, 8.35 mmol) (prepared according to example C), in DMF (10 mL) is added triethylamine (2.0 mL, 14.30 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with EtOAc (100 mL) and is washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate, concentrated and the resulting residue is purified by flash chromatography with 35% EtOAc in Hexane as the eluent to afford the desired 2-(2-amino-benzoylamino)-pentanoic acid methyl ester (575 mg, 50%).

Workup

  1. washis washed with H2O (50 mL×3)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe resulting residue is purified by flash chromatography with 35% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-9961f8439ccb4c409497c9d405100d90
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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