Triethylamine → (S)-2-(2-amino-5-methoxy-benzoylamino)-hexanoic acid methyl ester

HRID 388479Notes

Reaction equation

HRID 388479 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[C:7]2[C:8]([O:10]C(=O)[NH:12][C:6]2=[CH:5][CH:4]=1)=O.Cl.[CH3:16][O:17][C:18](=[O:25])[C@@H:19]([NH2:24])[CH2:20][CH2:21][CH2:22][CH3:23].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH3:16][O:17][C:18](=[O:25])[C@@H:19]([NH:24][C:8](=[O:10])[C:7]1[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=1[NH2:12])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2944796-methoxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

Product 1

HCID 68727802(S)-2-(2-amino-5-methoxy-benzoylamino)-hexanoic acid methyl esterYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-methoxy-isatoic anhydride (1.0 g, 5.18 mmol) and (S)-2-amino-hexanoic acid methyl ester hydrochloride (1.4 g, 7.71 mmol) (prepared according to example A) in DMF (10 mL) is added triethylamine (2.0 mL, 11.48 mmol). The mixture is stirred at room temperature for 16 hours. The reaction mixture is diluted with EtOAc (100 mL) and washed with H2O (50 mL×3). The organic layer is dried over sodium sulfate, concentrated and the residue is purified by flash chromatography with 60% EtOAc in Hexane as the eluent to afford (S)-2-(2-amino-5-methoxy-benzoylamino)-hexanoic acid methyl ester (410 mg, 27%).

Workup

  1. washwashed with H2O (50 mL×3)
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue is purified by flash chromatography with 60% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-b0d3c116923244c6922301272b5d72f6
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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