4-Toluenesulfonyl chloride → 5-Tosyloxymethyl-1,3-oxazolidine-2-one

HRID 2223010

반응식

HRID 2223010 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.CCN(CC)CC.[OH:19][CH2:20][CH:21]1[O:25][C:24](=[O:26])[NH:23][CH2:22]1>ClCCl>[S:7]([O:19][CH2:20][CH:21]1[O:25][C:24](=[O:26])[NH:23][CH2:22]1)([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 102907735-(Hydroxymethyl)oxazolidin-2-one

생성물 1

HCID 27937695-Tosyloxymethyl-1,3-oxazolidine-2-one수율 80%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

p-Toluenesulphonyl chloride (2.74 g, 14.36 mmol) and Et3N (1.45 g, 14.36 mmol) were added to 5-hydroxymethyl-1,3-oxazolidine-2-one (1.40 g, 11.97 mmol) dispersed in 20 mL of dichloromethane and stirred overnight at room temperature under N2. After completion of the reaction (TLC), the solvent in the reaction mixture was evaporated and the residue was purified by column chromatography employing EtOAc-hexane (70:30) as eluent to afford 5-tosyloxymethyl-1,3-oxazolidine-2-one in 80% yield. m.p. 96-99° C.; [α]27D=+45.40 CHCl3); IR (KBr) 3302, 2980, 2925, 2871, 1757, 1694, 1357, 1184, 1090, 996, 965 cm1; 1HNMR (200 MHz, CDCl3) δ 2.47 (s, 3H), 3.40-3.50 (m, 1H), 3.64-3.74 (m, 1H), 4.14 (d, 2H, J=4.4 Hz), 4.71-4.82 (m, 1H), 7.35 (d, 2H, J=8.2 Hz), 7.78 (d, 2H, J=8.2 Hz); Mass (EI) 271, 207, 173, 155, 139, 91.

후처리

  1. customAfter completion of the reaction (TLC)
  2. customthe solvent in the reaction mixture was evaporated
  3. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-ee0f40122a1f4cb58afa3bf550f298a1
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07374926B2

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