Water → p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester

HRID 2396888Notes

Reaction equation

HRID 2396888 reaction equation
C(N(CC)CC)C.[CH2:8]([C@H:15]1[C@@H:19]([CH2:20][OH:21])[O:18][C:17](=[O:22])[NH:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.O>CC(C)=O>[CH2:8]([C@H:15]1[C@@H:19]([CH2:20][O:21][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[O:18][C:17](=[O:22])[NH:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 9859125(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone

Product 1

HCID 56996730p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
22 °C

Procedure

5.6 ml of triethylamine are added at 22° C. to a stirred suspension of 5.55 g of the alcohol from Example 8 in 27 ml of acetone and 6.64 g of p-toluenesulphonyl chloride and stirred at 22° C. for 6.5 hours. The suspension is treated with water, stirred at 10° C., filtered, the residue is washed with a water/acetone solution (3:2) and dried to give 9.09 g (94.%) of 99% p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, m.p. 148.7°-150.3° C., [α]D20 : +3.0° (1% acetone).

Workup

  1. stirringstirred at 10° C.
  2. filtrationfiltered
  3. washthe residue is washed with a water/acetone solution (3:2)
  4. customdried

Sources & evidence

ORD record
ord-97f0e4a805e84bb599ba4123929947a7
Source dataset
uspto-grants-1996_02
Patent number
US05495025

Reaction notes

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