4-Nitrobenzenesulfonyl chloride → [(4S,5S)-4-benzyl-2-oxo-5-oxazolidinyl]methyl 4-nitrobenzenesulfonate

HRID 2396889Notes

Reaction equation

HRID 2396889 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:14]([C@H:21]1[C@@H:25]([CH2:26][OH:27])[O:24][C:23](=[O:28])[NH:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>C1COCC1.CN1CCOCC1>[CH2:14]([C@H:21]1[C@@H:25]([CH2:26][O:27][S:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)(=[O:11])=[O:12])[O:24][C:23](=[O:28])[NH:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 9859125(4S,5S)-5-hydroxymethyl-4-phenylmethyloxazolidinone

Product 1

HCID 11058277[(4S,5S)-4-benzyl-2-oxo-5-oxazolidinyl]methyl 4-nitrobenzenesulfonateYield 94.2%

Reagents, catalysts & solvents 2

HCID 79724-MethylmorpholineSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

15.4 g of p-nitrobenzenesulphonyl chloride are added in portions at 20°-25° C. to a stirred suspension of 12.0 g of the alcohol from Example 8 in 35 ml of THF and 7.66 ml of N-methylmorpholine and stirred for 4.5 hours. The suspension is again treated with 0.77 ml of N-methylmorpholine and stirred at 22° C. for 4.5 hours. The mixture is treated with 70 ml of a 2% sodium bicarbonate solution, stirred for 1.5 hours, filtered, the residue is washed with water and ethanol and dried to give 21.4 g (94%) of 98.5 % p-nitrobenzenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, m.p. 148°-149.5° C., [α]D20 : +10.0° (1% in acetone).

Workup

  1. stirringstirred at 22° C. for 4.5 hours
  2. stirringstirred for 1.5 hours
  3. filtrationfiltered
  4. washthe residue is washed with water and ethanol
  5. customdried

Sources & evidence

ORD record
ord-9c5fd1f06ede478897d5ede93cc57f97
Source dataset
uspto-grants-1996_02
Patent number
US05495025

Reaction notes

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