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

HRID 2223010Notes

Reaction equation

HRID 2223010 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-ee0f40122a1f4cb58afa3bf550f298a1
Source dataset
uspto-grants-2008_05
Patent number
US07374926B2

Reaction notes

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