Sulfuric acid magnesium salt (1:1) → 3-nitrooxypropyl (2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylate

HRID 1351420노트

반응식

HRID 1351420 반응식
[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@H:16]([C:18]([OH:20])=O)[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].[N+:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][NH:31]1)([O-:23])=[O:22].C([O-])(O)=O.[Na+].S([O-])([O-])(=O)=O.[Mg+2]>CCOC(C)=O.[Cl-].[Na+].O>[N+:21]([O:24][CH2:25][CH2:26][CH2:27][O:28][C:29](=[O:35])[C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[C:18](=[O:20])[C@H:16]([CH3:17])[NH:15][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([O-:23])=[O:22]

참가 물질

7

반응물 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 5702571N-[1(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanineHCID 11672975L-proline 3-nitrooxypropyl ester

생성물 1

HCID 116773433-nitrooxypropyl (2S)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylate수율 40.9%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매2회HCID 57417360Sodium chloride; water용매

실험 절차

To a suspension of 1,1-carbonylimidazole (22 g, 136 mmol) in EtOAc (150 mL) a solution of commercial N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanine (20.2 g, 72.32 mmol) in EtOAc (100 mL) was added dropwise in 10 minutes. The resulting solution was stirred at room temperature for 1 hour then L-proline 3-nitrooxypropyl ester (28.8 g, 113 mmol) was added and the mixture was stirred for 16 hours. Then was treated with saturated NaHCO3 and brine. The organic layer was anhydrified with magnesium sulphate and concentrated. The residue was purified by flash chromatography (nHexane/EtOAc 4:6) affording N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline 3-nitrooxypropyl ester (14.2 g, 26%) as a pale yellow oil.

후처리

  1. additionwas added dropwise in 10 minutes
  2. stirringthe mixture was stirred for 16 hours
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (nHexane/EtOAc 4:6)

출처 및 근거

ORD 기록
ord-abecd63970f94866a4fdd07e72aa2ee9
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217733B2

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