Nitrogen → Methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester

HRID 42785노트

반응식

HRID 42785 반응식
N#N.[CH3:3][C:4]1([C:9]2[N:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1.CCN(CC)CC.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:3][C:4]1([C:9]2[N:14]=[C:13]([CH2:15][O:16][S:24]([CH3:27])(=[O:26])=[O:25])[CH:12]=[CH:11][CH:10]=2)[O:5][CH2:6][CH2:7][O:8]1

참가 물질

7

반응물 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66928639[6-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-methanol

생성물 1

HCID 86649482Methanesulfonic acid 6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [6-(2-methyl-[1,3]dioxolan-2-yl)-pyridin-2-yl]-methanol (729 mg, 3.74 mmol) in dry CH2Cl2 (10.0 mL) was treated at 0° C. with Et3N (0.67 mL, 4.83 mmol) followed by DMAP (46 mg, 0.37 mmol) and Ms-Cl (0.37 mL, 4.72 mmol). After stirring at 0° C. for 1 h, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (70:30 to 50:50 hept-EA) gave the title compound as a pale yellow oil. LC-MS-conditions 02: tR=0.79 min; [M+H]+=274.39.

후처리

  1. customthe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with CH2Cl2 (10 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (70:30 to 50:50 hept-EA)

출처 및 근거

ORD 기록
ord-4758c3e68a7d43f888e55d711618913e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536209B2

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