HCID 11778479, compound → HCID 10357282, compound

HRID 481793Notes

Reaction equation

HRID 481793 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([N:9]2[C@@H:11]([CH:12]([CH3:14])[CH3:13])[C@H:10]2[C:15]([O:17][CH3:18])=[O:16])=[O:8])=[CH:3][CH:2]=1.C(OCC)(=[O:22])C.CCCCC>>[C:1]1([CH3:19])[CH:2]=[CH:3][C:4]([S:7]([N:9]2[C@@H:11]([CH:12]([CH3:14])[CH3:13])[C@H:10]2[C:15]([O:17][CH3:18])=[O:16])(=[O:22])=[O:8])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 11778479HCID 11778479, compoundHCID 22335286Ethyl acetate pentane

Product 1

HCID 10357282HCID 10357282, compoundYield 95%

Procedure

Following the procedure of Example 11A, but replacing the (2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine with (2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-isopropylaziridine (prepared according to Example 4), and performing the flash chromatography with ethyl acetate:n-pentane (2:8) as the eluent afforded the titled compound (0.565 g, 95%): mp 52°-4° C.; [α]D20 -34.3° (c 1.2, CHCl3); IR (KBr): 2963.9, 1755.8, 1597.5, 1209.6 1102.1, 1091.4 cm-1 ; 1H NMR (CDCl3) δ0.84 (d, J=6.6 Hz 3H), 0.89 (d, J=6.8 Hz, 3H), 1.57-1.68 (m 1H), 2.45 (s, 3H), 2.68 (dd, J=7.6 Hz, 9.9 Hz, 1H), 3.45 (d, J=7.44 Hz, 1H),3.74 (s, 3H), 7.35 (d, J=8.2 Hz, 2H), 7.86 (d, J=8.3 Hz, 2H); 13C NMR (CDCl3) δ145.0, 134.0, 129.7, 128.3, 52.6, 50.8, 41.1, 26.7, 21.6, 20.5, 18.9. Anal. Calcd for C14H19 NO4S: C, 56.55; H, 6.44. Found: C, 56.36; H, 6.63.

Sources & evidence

ORD record
ord-daaa99ea33d14bcdb39aded8221a1eb3
Source dataset
uspto-grants-1998_08
Patent number
US05789599

Reaction notes

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