反応式
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.C(=O)([O-])O.[Na+].ON1C(=O)CCC1=O.[C:23]([O:27][C:28]([NH:30][CH2:31][C:32]([OH:34])=O)=[O:29])([CH3:26])(C)C.[C:35](O)(=O)[CH2:36][C:37]([CH2:42][C:43](O)=O)(C(O)=O)O>O.O1CCOCC1>[CH2:23]([O:27][C:28]([NH:30][CH2:31][C:32]([N:5]1[CH2:6][C@H:2]([OH:1])[CH2:3][C@H:4]1[C:7]([OH:9])=[O:8])=[O:34])=[O:29])[C:26]1[CH:43]=[CH:42][CH:37]=[CH:36][CH:35]=1参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
3,4-Dehydroproline 1 (0.011 g, 0.097 mmol) and sodium hydrogen carbonate (0.0082 g, 0.097 mmol) were dissolved in water (1 cm3). A solution of N-tert-butyloxycarbonylglycine N-hydroxysuccinimide 2 (0.024 g, 0.088 mmol) in dioxane (1 cm3) was added dropwise and stirred overnight. The reaction mixture was diluted with water, acidified with solid citric acid and extracted with dichloromethane (3×). The combined organic layers were dried (MgSO4), filtered and the solvent removed to afford crude acid 3 (0.0242 g, ca. 100%) that was used without further purification. Acid 3 was shown to be a 75:25 trans:cis mixture of conformers by 1H NMR analysis (the ratio was estimated from the integration of the Proα protons at δ 5.21 and 5.13 of the major and minor conformers respectively): δH (300 MHz; CDCl3; Me4Si) 1.411 [2.25H, s, C(CH3)3], 1.42 [6.75H, s, C(CH3)3], 3.83-4.08 (2H, m, Glyα-H2), 4.25-4.45 (2H, m, Proδ-H2), 5.13* (0.25H, br d, J 2.8, Pros-H), 5.21 (0.75H, br d, J 3.1, Proα-H), 5.55-5.80 (2H, br m, O—H and N—H) and 5.86-6.02 (2H, m, Proβ-H and Proγ-H).
後処理
- extractionextracted with dichloromethane (3×)
- dry with materialThe combined organic layers were dried (MgSO4)
- filtrationfiltered
- customthe solvent removed
出典と根拠
- ORDレコード
- ord-91cfb877ddec4ee8a3ea2174fa2ecf2a
- 出典データセット
- uspto-grants-2011_01
- 特許番号
- US07863304B2
関連ノート
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