Dimethyl Sulfoxide → Biphenyl-2-ylcarbamic Acid 1-[2-(3-formylbenzylcarbamoyl)ethyl]piperidin-4-yl Ester

HRID 13859

반응식

HRID 13859 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][CH:36]=1)[CH2:6][NH:7][C:8]([CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19](=[O:33])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:14][CH2:13]1)=[O:9].CCN(C(C)C)C(C)C.CS(C)=O.N1C=CC=CC=1.S(=O)(=O)=O>C(Cl)Cl>[CH:2]([C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][CH:36]=1)[CH2:6][NH:7][C:8]([CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([O:18][C:19](=[O:33])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:16][CH2:17]1)=[O:9])=[O:1]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 168533Sulfur trioxide-pyridineHCID 59340333Biphenyl-2-ylcarbamic acid 1-[2-(3-hydroxymethylbenzylcarbamoyl)ethyl]piperidin-4-yl Ester

생성물 1

HCID 59340336Biphenyl-2-ylcarbamic Acid 1-[2-(3-formylbenzylcarbamoyl)ethyl]piperidin-4-yl Ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

To a flask was added biphenyl-2-ylcarbamic acid 1-[2-(3-hydroxymethylbenzyl carbamoyl)ethyl]piperidin-4-yl ester (0.33 g, 0.68 mmol; prepared as described in Preparation 12), DCM (5 mL), DIPEA (0.47 mL, 2.7 mol) and DMSO (0.2 mL, 2.7 mol). Using an ice bath, the mixture was cooled to about −10° C. and sulfur trioxide pyridine-complex (0.32 g, 2.0 mol) was added. The reaction was stirred at −10° C. for 0.75 hour. Before removing the ice-bath, the reaction was quenched by adding water (5 mL). The aqueous layer was separated and the organic layer was washed with water (2×5 mL), 1.0N NaHSO4(aq) (2×5 mL), 1.0N NaHCO3(aq) (1×5 mL) and brine (0.5 L) and then dried over MgSO4 and filtered to provide the title compound which was used without further purification.

후처리

  1. customBefore removing the ice-bath
  2. customthe reaction was quenched
  3. additionby adding water (5 mL)
  4. customThe aqueous layer was separated
  5. washthe organic layer was washed with water (2×5 mL), 1.0N NaHSO4(aq) (2×5 mL), 1.0N NaHCO3(aq) (1×5 mL) and brine (0.5 L)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered

출처 및 근거

ORD 기록
ord-3573a0cdb97e4cd3a4de80ec06e41875
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728144B2

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