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

HRID 388479

반응식

HRID 388479 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b0d3c116923244c6922301272b5d72f6
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377949B2

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