反応式
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[NH2:23][C@@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@H:25]1[OH:30].C(N(CC)CC)C>C(Cl)Cl.O.CN(C=O)C>[OH:30][C@@H:25]1[CH2:26][CH2:27][CH2:28][CH2:29][C@H:24]1[NH:23][C:14]([CH:10]1[O:11][CH2:12][CH2:13][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9]1)=[O:16]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 3
実験手順
To a mixture of 4-(phenylmethyl)-2-morpholinecarboxylic acid (5 g, 22.60 mmol) and DMF (0.1 mL) in CH2Cl2 (113 mL) was added oxalyl chloride (2.97 mL, 33.9 mmol) at 25° C. The mixture was stirred at this temperature for 1 hour and the mixture turned clear. The solvent and excess of oxalyl chloride were removed in vacuo, and the resulting residue was dissolved in CH2Cl2 (113 mL). (1R,2R)-2-Aminocyclohexanol (2.60 g, 22.60 mmol) and triethylamine (12.60 mL, 90 mmol) were added, and the resulting mixture was stirred overnight. Water (80 mL) was added to quench the reaction. the organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×80 mL). The combined organics were washed with sat. NaHCO3(aq) (80 mL), then brine (2×80 mL), dried (MgSO4), and evaporated to afford the title compound (5.3 g). LC-MS (ES) m/z=319 [M+H]+.
後処理
- customThe solvent and excess of oxalyl chloride were removed in vacuo
- dissolutionthe resulting residue was dissolved in CH2Cl2 (113 mL)
- stirringthe resulting mixture was stirred overnight
- customto quench
- customthe reaction
- customthe organic layer was separated
- extractionthe aqueous layer was extracted with CH2Cl2 (2×80 mL)
- washThe combined organics were washed with sat. NaHCO3(aq) (80 mL)
- dry with materialbrine (2×80 mL), dried (MgSO4)
- customevaporated
出典と根拠
- ORDレコード
- ord-90fe2358a9b748329b0dcc83ddab5694
- 出典データセット
- uspto-grants-2014_04
- 特許番号
- US08697685B2
関連ノート
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