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

HRID 388479

反応式

HRID 388479 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-b0d3c116923244c6922301272b5d72f6
出典データセット
uspto-grants-2013_02
特許番号
US08377949B2

関連ノート

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