Triethylamine → HCID 58504731, 화합물

HRID 2367335

반응식

HRID 2367335 반응식
[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

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 21637HCID 21637, 화합물HCID 65578Oxalyl chlorideHCID 27763534-Benzylmorpholine-2-carboxylic acid

생성물 1

HCID 58504731HCID 58504731, 화합물수율 125.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-2117ddf72c944496b061ad78302a4f5a
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

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