Triethylamine → HCID 58504731、化合物

HRID 2367335

反応式

HRID 2367335 の反応式
[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][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)=[O:26].C(N(CC)CC)C>C(Cl)Cl.O.CN(C=O)C>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:25](=[O:26])[CH2:24][NH:23][C:14]([CH:10]2[O:11][CH2:12][CH2:13][N:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:9]2)=[O:16])=[CH:32][CH:31]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 21637HCID 21637、化合物HCID 65578Oxalyl chlorideHCID 27763534-Benzylmorpholine-2-carboxylic acid

生成物 1

HCID 58504731HCID 58504731、化合物収率 125.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 4-(phenylmethyl)-2-morpholinecarboxylic acid (1.61 g, 7.28 mmol) and DMF (0.1 mL) in CH2Cl2 (70 mL) was added oxalyl chloride (0.956 mL, 10.92 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 (70 mL). 2-Amino-1-(4-chlorophenyl)ethanone (1.5 g, 7.28 mmol) and triethylamine (4.06 mL, 29.1 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 get 3.4 g yellow residue, which was chromatographed (EtOAc-petroleum ether, 1:1) to afford the title compound (2.5 g). LC-MS (ES) m/z=373 [M+H]+.

後処理

  1. customThe solvent and excess of oxalyl chloride were removed in vacuo
  2. dissolutionthe resulting residue was dissolved in CH2Cl2 (70 mL)
  3. stirringthe resulting mixture was stirred overnight
  4. customto quench
  5. customthe reaction
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (2×80 mL)
  8. washThe combined organics were washed with sat. NaHCO3 aq. (80 mL)
  9. dry with materialbrine (2×80 mL), dried (MgSO4)
  10. customevaporated

出典と根拠

ORDレコード
ord-2117ddf72c944496b061ad78302a4f5a
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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