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 1351420ノート

反応式

HRID 1351420 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-abecd63970f94866a4fdd07e72aa2ee9
出典データセット
uspto-grants-2007_05
特許番号
US07217733B2

反応ノート

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