Isatoic Anhydride → (S)-(2-amino-benzoylamino)-phenyl-acetic acid methyl ester

HRID 388458Notes

Reaction equation

HRID 388458 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:25])[C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH2:18].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH3:14][O:15][C:16](=[O:25])[C@@H:17]([NH:18][C:2](=[O:4])[C:1]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:6])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 8359Isatoic AnhydrideHCID 8471TriethylamineHCID 11217910(S)-(+)-2-Phenylglycine methyl ester hydrochloride

Product 1

HCID 68727988(S)-(2-amino-benzoylamino)-phenyl-acetic acid methyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of isatoic anhydride (250 mg, 1.53 mmol) and (S)-2-phenylglycine methyl ester hydrochloride (370 mg, 1.84 mmol) in DMF (5.0 mL) is added triethylamine (0.29 mL, 2.07 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 and concentrated to afford (S)-(2-amino-benzoylamino)-phenyl-acetic acid methyl ester (330 mg, 76%).

Workup

  1. washis washed with H2O (50 mL×3)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7f0bddedd0c845c9be728cd5e0743626
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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