m-Chloroperbenzoic acid → HCID 10042330, compound

HRID 481792Notes

Reaction equation

HRID 481792 reaction equation
[C:1]1([CH3:22])[CH:6]=[CH:5][C:4]([S:7]([N:9]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@H:10]2[C:18]([O:20][CH3:21])=[O:19])=[O:8])=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:28]>C(Cl)(Cl)Cl>[C:1]1([CH3:22])[CH:2]=[CH:3][C:4]([S:7]([N:9]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@H:10]2[C:18]([O:20][CH3:21])=[O:19])(=[O:28])=[O:8])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10245181HCID 10245181, compound

Product 1

HCID 10042330HCID 10042330, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into a 25-mL single-necked round-bottomed flask equipped with a magnetic stir bar were placed 0.63 g (2.0 mmol) of (2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine (prepared according to Example 1), 1.04 g (3.0 mmol) 3-chloroperoxybenzoic acid (60%, from Aldrich) and 20 mL chloroform. The reaction mixture was stirred at room temperature for 1 h, washed with 20 mL saturated aqueous Na2S2O3 solution, diluted with 50 mL CH2Cl2, washed with saturated aqueous Na2CO3 solution (2×10 mL) and dried (MgSO4). Filtration and removal of the solvent gave a solid residue which was purified by flash chromatography (ethyl acetate:n-pentane, 2:8) to afford the titled compound (0.62 g, 94%): mp. 85°-87° C.; [α]D20 +18.2° (c 1.0, CHCl3); IR (KBr): 3033.3, 1757.2, 1597.5, 1334.1, 1210.1, 1163.6, 1091.7 cm-1 ; 1H NMR (CDCl3) δ2.44 (s, 3H, CH3), 3.49 (s, 3H, CH3), 3.71 (d, J=7.7 Hz, 1H, CH), 4.12 (d, J=7.6 Hz, 1H, CH), 7.20-7.32 (m, 5H, aromatic), 7.35 (d, J=8.4 Hz, 2H, aromatic), 7.92 (d, J=8.3 Hz, 2H, aromatic); 13C NMR (CDCl3) δ164.5, 145.0, 133.8, 130.9, 129.7, 128.3, 128.0, 127.9, 127.2, 52.3, 45.3, 43.3, 21.6. Anal. Calcd for C17H17NO4S: C, 61.61; H, 5.17. Found: C, 61,43; H, 5.17.

Workup

  1. customInto a 25-mL single-necked round-bottomed flask equipped with a magnetic stir bar
  2. washwashed with 20 mL saturated aqueous Na2S2O3 solution
  3. additiondiluted with 50 mL CH2Cl2
  4. washwashed with saturated aqueous Na2CO3 solution (2×10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and removal of the solvent
  7. customgave a solid residue which
  8. customwas purified by flash chromatography (ethyl acetate:n-pentane, 2:8)

Sources & evidence

ORD record
ord-9a54d4023dcf41ceb7c896f119f454ae
Source dataset
uspto-grants-1998_08
Patent number
US05789599

Reaction notes

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